Skip to main content
SpringerLink
Log in

Advances in theoretical study on transition-metal-catalyzed C−H activation

  • Reviews
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

Transition-metal-catalyzed C–H activation represents one of most attractive research fields in modern organic chemistry while theoretical studies have become a popular and effective tool for elucidating mechanism nowadays. The recent achievements in the cross field of the two orientations are reviewed in this article. The first part introduced the advances in theoretical study on transition-metal-catalyzed C–H activation. The elegant work reported mainly in and after 2013, classified according to the mechanisms of C–H activation, were covered. The second part provided an analysis on the distribution of quantum-chemical methods, solvation models and basis sets in the collected theoretical studies.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Balcells D, Clot E, Eisenstein O, Nova A, Perrin L. Acc Chem Res, 2016, 49: 1070–1078

    Article  CAS  Google Scholar 

  2. Gensch T, Hopkinson MN, Glorius F, Wencel-Delord J. Chem Soc Rev, 2016, 45: 2900–2936

    Article  CAS  Google Scholar 

  3. Shi ZJ. Sci China Chem, 2015, 58, 1245–1248

    Article  CAS  Google Scholar 

  4. Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew Chem Int Ed, 2012, 51: 10236–10254

    Article  CAS  Google Scholar 

  5. Engle KM, Mei TS, Wasa M, Yu J. Acc Chem Res, 2012, 45: 788–802

    Article  CAS  Google Scholar 

  6. Cook AK, Schimler SD, Matzger AJ, Sanford MS. Science, 2016, 351: 1421–1424

    Article  CAS  Google Scholar 

  7. Zhang FL, Hong K, Li TJ, Park H, Yu JQ. Science, 2016, 351: 252–256

    Article  CAS  Google Scholar 

  8. Wei H, Lu H, Fang T, Bo Z. Sci China Chem, 2015, 58: 286–293

    Article  CAS  Google Scholar 

  9. Pan C, Han J, Zhu C. Sci China Chem, 2014, 57, 1172–1175

    Article  CAS  Google Scholar 

  10. Sharma A, Hartwig JF. Nature, 2015, 517: 600–604

    Article  CAS  Google Scholar 

  11. Liu YJ, Xu H, Kong WJ, Shang M, Dai HX, Yu JQ. Nature, 2014, 515: 389–393

    Article  CAS  Google Scholar 

  12. Wang B, He G, Chen G. Sci China Chem, 2015, 58: 1345–1348

    Article  CAS  Google Scholar 

  13. Shi Y, Wang Z, Cheng Y, Lan J, She Z, You J. Sci China Chem, 2015, 58: 1292–1296

    Article  CAS  Google Scholar 

  14. Cheng C, Hartwig JF. Science, 2014, 343: 853–857

    Article  CAS  Google Scholar 

  15. Ackermann L. Chem Rev, 2011, 111: 1315–1345

    Article  CAS  Google Scholar 

  16. Caballero A. Pérez PJ. Chem Soc Rev, 2013, 42: 8809–8820

    Article  CAS  Google Scholar 

  17. Musaev DG, Figg TM, Kaledin, AL. Chem Soc Rev, 2014, 43: 5009–5031

    Article  CAS  Google Scholar 

  18. Huang Z, Lim HN, Mo FY, Young MC, Dong G. Chem Soc Rev, 2015, 44: 7764–7786

    Article  CAS  Google Scholar 

  19. Vanjari R, Singh KN. Chem Soc Rev, 2015, 44: 8062–8096

    Article  CAS  Google Scholar 

  20. Huang H, Ji X, Wu W, Jiang H. Chem Soc Rev, 2015, 44: 1155–1171

    Article  CAS  Google Scholar 

  21. Lu X, Xiao B, Shang R, Liu L. Chin Chem Lett, 2016, 27: 305–311

    Article  CAS  Google Scholar 

  22. Zhang F, Spring DR. Chem Soc Rev, 2014, 43: 6906–6919

    Article  CAS  Google Scholar 

  23. Arockiam PB, Bruneau C, Dixneuf PH. Chem Rev, 2012, 112: 5879–5918

    Article  CAS  Google Scholar 

  24. Manikandan R, Jeganmohan M. Org Biomol Chem, 2015, 13: 10420–10436

    Article  CAS  Google Scholar 

  25. Song G, Wang F, Li X. Chem Soc Rev, 2012, 41: 3651–3678

    Article  CAS  Google Scholar 

  26. Lombard FJ, Coster MJ. Org Biomol Chem, 2015, 13: 6419–6431

    Article  CAS  Google Scholar 

  27. Xie J, Pan C, Abdukader A, Zhu C. Chem Soc Rev, 2014, 43: 5245–5256

    Article  CAS  Google Scholar 

  28. Wang JB. Sci China Chem, 2014, 57: 1057

    Article  CAS  Google Scholar 

  29. Thapa S, Shrestha B, Gurung SK, Giri R. Org Biomol Chem, 2015, 13: 4816–4827

    Article  CAS  Google Scholar 

  30. Gunay A, Theopold, KH. Chem Rev, 2010, 110: 1060–1081

    Article  CAS  Google Scholar 

  31. Colby, DA. Bergman RG, Ellman JA. Chem Rev 2010, 110: 624–655

    Article  CAS  Google Scholar 

  32. Qi X, Chen P, Liu G. Sci China Chem, 2015, 58: 1249–1251

    Article  CAS  Google Scholar 

  33. Rao Y, Shan G, Yang X. Sci China Chem, 2014, 57: 930–944

    Article  CAS  Google Scholar 

  34. Lyons TW, Sanford MS. Chem Rev, 2010, 110: 1147–1169

    Article  CAS  Google Scholar 

  35. Li BJ, Shi ZJ. Chem Soc Rev, 2012, 41: 5588–5598

    Article  CAS  Google Scholar 

  36. Li B, Dixneuf PH. Chem Soc Rev, 2013, 42: 5744–5767

    Article  CAS  Google Scholar 

  37. Mkhalid IAI, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem Rev 2010, 110: 890–931

    Article  CAS  Google Scholar 

  38. Yang J. Org Biomol Chem, 2015, 13: 1930–1941

    Article  CAS  Google Scholar 

  39. Yang Y, Wang C. Sci China Chem, 2015, 58: 1266–1279

    Article  CAS  Google Scholar 

  40. Wang K, Hu F, Zhang Y, Wang J. Sci China Chem, 2015, 58: 1252–1265

    Article  CAS  Google Scholar 

  41. Cho SH, Kim JY, Kwak J, Chang S. Chem Soc Rev, 2011, 40: 5068–5083

    Article  CAS  Google Scholar 

  42. Louillat ML, Patureau FW. Chem Soc Rev, 2014, 43: 901–910

    Article  CAS  Google Scholar 

  43. Ros A, Fernández R, Lassaletta JM. Chem Soc Rev, 2014, 43: 3229–3243

    Article  CAS  Google Scholar 

  44. Liu C, Yuan J, Gao M, Tang S, Li W, Shi R, Lei A. Chem Rev, 2015, 115: 12138–12204

    Article  CAS  Google Scholar 

  45. Liu C, Zhang H, Shi W, Lei A. Chem Rev, 2011, 111: 1780–1824

    Article  CAS  Google Scholar 

  46. Cho KB, Hirao H, Shaik S, Nam W. Chem Soc Rev, 2016, 45: 1197–1210

    Article  CAS  Google Scholar 

  47. Park Y, Ahn S, Kang D, Baik MH. Acc Chem Res, 2016, 49: 1263–1270

    Article  CAS  Google Scholar 

  48. Gagnon N, Tolman WB. Acc Chem Res, 2015, 48: 2126–2131

    Article  CAS  Google Scholar 

  49. McCann SD, Stahl SS. Acc Chem Res, 2015, 48: 1756–1766

    Article  CAS  Google Scholar 

  50. Nam W, Lee YM, Fukuzumi S. Acc Chem Res, 2014, 47: 1146–1154

    Article  CAS  Google Scholar 

  51. Simmons EM, Hartwig JF. Angew Chem Int Ed, 2012, 51: 2–9

    Article  CAS  Google Scholar 

  52. Copéret C. Chem Rev, 2010, 110: 656–680

    Article  CAS  Google Scholar 

  53. Zhao S, Chen FJ, Liu B, Shi BF. Sci China Chem, 2015, 58: 1302–1309

    Article  CAS  Google Scholar 

  54. Xiao B, Fu Y, Xu J, Gong TJ, Dai JJ, Yi J, Liu L. J Am Chem Soc, 2010, 132: 468–469

    Article  CAS  Google Scholar 

  55. Yu YB, Wang Z, Zhang XG. Sci China Chem, 2014, 57: 276–281

    Article  CAS  Google Scholar 

  56. Li Y, Li BJ, Wang WH, Huang WP, Zhang XS, Chen K, Shi ZJ. Angew Chem Int Ed, 2011, 50: 2115–2119

    Article  CAS  Google Scholar 

  57. Zheng J, Wang SB, Zheng C, You SL. J Am Chem Soc, 2015, 137: 4880–4883

    Article  CAS  Google Scholar 

  58. Li W, Duan Z, Zhang X, Zhang H, Wang M, Jiang R, Zeng H, Liu C, Lei A. Angew Chem Int Ed, 2015, 54: 1893–1896

    Article  CAS  Google Scholar 

  59. Li Q, Yu ZX. J Am Chem Soc, 2010, 132: 4542–4543

    Article  CAS  Google Scholar 

  60. Hu Z, Luo S, Zhu Q. Sci China Chem, 2015, 58: 1349–1353

    Article  CAS  Google Scholar 

  61. Xu J, Fu Y, Luo DF, Jiang YY, Xiao B, Liu ZJ, Gong TJ, Liu L. J Am Chem Soc, 2011, 133: 15300–15303

    Article  CAS  Google Scholar 

  62. Shi XY, Dong XF, Fan J, Liu KY, Wei JF, Li CJ. Sci China Chem, 2015, 58: 1286–1291

    Article  CAS  Google Scholar 

  63. Sun J, Wang F, Shen Y, Zhi H, Wu H, Liu Y. Org Biomol Chem, 2015, 13: 10236–10243

    Article  CAS  Google Scholar 

  64. Boller TM, Murphy JM, Hapke M, Ishiyama T, Miyaura N, Hartwig JF. J Am Chem Soc, 2005, 127: 14263–14278

    Article  CAS  Google Scholar 

  65. Plata RE, Singleton DA. J Am Chem Soc, 2015, 137: 3811–3826

    Article  CAS  Google Scholar 

  66. Balcells D, Clot E, Eisenstein O. Chem Rev, 2010, 110: 749–823

    Article  CAS  Google Scholar 

  67. Bonney KJ, Schoenebeck F. Chem Soc Rev, 2014, 43: 6609–6638

    Article  CAS  Google Scholar 

  68. Houk KN. Chem Soc Rev, 2014, 43: 4905

    Article  CAS  Google Scholar 

  69. Sperger T, Sanhueza IA, Kalvet I, Schoenebeck F. Chem Rev, 2015, 115: 9532–9586

    Article  CAS  Google Scholar 

  70. Cheng GJ, Zhang X, Chung LW, Xu L, Wu YD. J Am Chem Soc, 2015, 137: 1706–1725

    Article  CAS  Google Scholar 

  71. Zhang X, Chung LW, Wu YD. Acc Chem Res, 2016, 49: 1302–1310

    Article  CAS  Google Scholar 

  72. Gorelsky SI, Lapointe D, Fagnou K. J Am Chem Soc, 2008, 130: 10848–10849

    Article  CAS  Google Scholar 

  73. Boutadla Y, Davies DL, Macgregor SA, Poblador-Bahamonde AI. Dalton Trans, 2009: 5820–5831

    Google Scholar 

  74. Holstein PM, Vogler M, Larini P, Pilet G, Clot E, Baudoin O. ACS Catal, 2015, 5: 4300–4308

    Article  CAS  Google Scholar 

  75. Xiao B, Gong TJ, Liu ZJ, Liu JH, Luo DF, Xu J, Liu L. J Am Chem Soc, 2011, 133: 9250–9253

    Article  CAS  Google Scholar 

  76. Yang YM, Dang ZM, Yu HZ. Org Biomol Chem, 2016, 14: 4499–4506

    Article  CAS  Google Scholar 

  77. Sanhueza IA, Wagner AM, Sanford MS, Schoenebeck F. Chem Sci, 2013, 4: 2767–2775

    Article  CAS  Google Scholar 

  78. Zhang Q, Yu H, Fu Y. Sci China Chem, 2015, 58: 1316–1322

    Article  CAS  Google Scholar 

  79. Smalley AP, Gaunt MJ. J Am Chem Soc, 2015, 137: 10632–10641

    CAS  Google Scholar 

  80. Zhang S, Shi L, Ding Y. J Am Chem Soc, 2011, 133: 20218–20229

    Article  CAS  Google Scholar 

  81. Dang Y, Deng X, Guo J, Song C, Hu W, Wang ZX. J Am Chem Soc, 2016, 138: 2712–2723

    Article  CAS  Google Scholar 

  82. Zhang L, Fang DC. Org Biomol Chem, 2015, 13: 7950–7960

    Article  CAS  Google Scholar 

  83. Xiao B, Gong TJ, Xu J, Liu ZJ, Liu L. J Am Chem Soc, 2011, 133: 1466–1474

    Article  CAS  Google Scholar 

  84. Cheng GJ, Chen P, Sun TY, Zhang X, Yu JQ, Wu YD. Chem Eur J, 2015, 21: 11180–11188

    Article  CAS  Google Scholar 

  85. Cotton FA, Koshevoy IO, Lahuerta P, Murillo CA. Sanaú M, Ubeda MA, Zhao Q. J Am Chem Soc, 2006, 128: 13674–13675

    Article  CAS  Google Scholar 

  86. Giri R, Lan Y, Liu P, Houk KN, Yu JQ. J Am Chem Soc, 2012, 134: 14118–14126

    Article  CAS  Google Scholar 

  87. Yang YF, Cheng GJ, Liu P, Leow D, Sun TY, Chen P, Zhang X, Yu JQ, Wu YD, Houk KN. J Am Chem Soc, 2014, 136: 344–355

    Article  CAS  Google Scholar 

  88. Anand M, Sunoj RB, Schaefer HF. ACS Catal, 2016, 6: 696–708

    Article  CAS  Google Scholar 

  89. Ruan GY, Qi ZH, Zhang Y, Liu W, Wang Y. RSC Adv, 2016, 6: 35855–35858

    Article  CAS  Google Scholar 

  90. Du L, Xu Y, Yang S, Li J, Fu X. J Org Chem, 2016, 81: 1921–1929

    Article  CAS  Google Scholar 

  91. Liu T, Zheng XW, Han LL, Li YP, Han SM, Yu ZY. RSC Adv, 2016, 6: 23265–23271

    Article  CAS  Google Scholar 

  92. Quiñones N, Seoane A, García-Fandiño R, Mascareñas JL, Gulías M. Chem Sci, 2013, 4: 2874–2879

    Article  CAS  Google Scholar 

  93. Algarra AG, Cross WB, Davies DL, Khamker Q, Macgregor SA. McMullin CL, Singh K. J Org Chem, 2014, 79: 1954–1970

    Article  CAS  Google Scholar 

  94. Liu L, Wu Y, Wang T, Gao X, Zhu J, Zhao Y. J Org Chem, 2014, 79: 5074–5081

    Article  CAS  Google Scholar 

  95. Fu R, Nielsen RJ, Goddard WA, Fortman GC, Gunnoe TB. ACS Catal, 2014, 4: 4455–4465

    Article  CAS  Google Scholar 

  96. Li J, Qiu Z. J Org Chem, 2015, 80: 10686–10693

    Article  CAS  Google Scholar 

  97. Herbert MB, Suslick BA, Liu P, Zou L, Dornan PK, Houk KN, Grubbs RH. Organometallics, 2015, 34: 2858–2869

    Article  CAS  Google Scholar 

  98. Wu J, Xu W, Yu ZX, Wang J. J Am Chem Soc, 2015, 137: 9489–9496

    Article  CAS  Google Scholar 

  99. Shan C, Luo X, Qi X, Liu S, Li Y, Lan Y. Organometallics, 2016, 35: 1440–1445

    Article  CAS  Google Scholar 

  100. Liu D, Yu H, Fu Y. Acta Chim Sinica, 2013, 71: 1385–1395

    Article  CAS  Google Scholar 

  101. Cross WB, Razak S, Singh K, Warner AJ. Chem Eur J, 2014, 20: 13203–13209

    Article  CAS  Google Scholar 

  102. Pahls DR, Allen KE, Goldberg KI, Cundari TR. Organometallics, 2014, 33: 6413–6419

    Article  CAS  Google Scholar 

  103. Tang SY, Gong TJ, Fu Y. Sci China Chem, 2013, 56: 619–632

    Article  CAS  Google Scholar 

  104. Gray A, Tsybizova A, Roithov J. Chem Sci, 2015, 6: 5544–5553

    Article  CAS  Google Scholar 

  105. Ruan GY, Zhang Y, Qi ZH, Ai DX, Liu W, Wang Y. Comput Theor Chem, 2015, 1054: 16–21

    Article  CAS  Google Scholar 

  106. Qi X, Zhang H, Shao A, Zhu L, Xu T, Gao M, Liu C, Lan Y. ACS Catal, 2015, 5: 6640–6647

    Article  CAS  Google Scholar 

  107. Figg TM, Park S, Park J, Chang S, Musaev DG. Organometallics, 2014, 33: 4076–4085

    Article  CAS  Google Scholar 

  108. Hong X, Liang Y, Houk KN. J Am Chem Soc, 2014, 136: 2017–2025

    Article  CAS  Google Scholar 

  109. Lu Q, Yu H, Fu Y. J Am Chem Soc, 2014, 136: 8252–8260

    Article  CAS  Google Scholar 

  110. Xu ZY, Jiang YY, Yu HZ, Fu Y. Chem Asian J, 2015, 10: 2479–2483

    Article  CAS  Google Scholar 

  111. Xu L, Zhu Q, Huang G, Cheng B, Xia Y. J Org Chem, 2012, 77: 3017–3024

    Article  CAS  Google Scholar 

  112. Guo W, Xia Y. J Org Chem, 2015, 80: 8113–8121

    Article  CAS  Google Scholar 

  113. Chen WJ, Lin Z. Organometallics, 2015, 34: 309–318

    Article  CAS  Google Scholar 

  114. Yang YF, Houk KN, Wu YD. J Am Chem Soc, 2016, 138: 6861–6868

    Article  CAS  Google Scholar 

  115. Zhou T, Guo W, Xia Y. Chem Eur J, 2015, 21: 9209–9218

    Article  CAS  Google Scholar 

  116. Guo W, Zhou T, Xia Y. Organometallics, 2015, 34: 3012–3020

    Article  CAS  Google Scholar 

  117. Chen J, Guo W, Xia Y. J Org Chem, 2016, 81: 2635–2638

    Article  CAS  Google Scholar 

  118. Yu S, Liu S, Lan Y, Wan B, Li X. J Am Chem Soc, 2015, 137: 1623–1631

    Article  CAS  Google Scholar 

  119. Wang Q, Li Y, Qi Z, Xie F, Lan Y, Li X. ACS Catal, 2016, 6: 1971–1980

    Article  CAS  Google Scholar 

  120. Gao B, Liu S, Lan Y, Huang H. Organometallics, 2016, 35: 1480–1487

    Article  CAS  Google Scholar 

  121. Lu Q, Yu H, Fu Y. Chem Commun, 2013, 49: 10847–10849

    Article  CAS  Google Scholar 

  122. Jiang J, Yu JQ, Morokuma K. ACS Catal, 2015, 5: 3648–3661

    Article  CAS  Google Scholar 

  123. Jiang J, Ramozzi R, Morokuma K. Chem Eur J, 2015, 21: 11158–11164

    Article  CAS  Google Scholar 

  124. Ruiz S, Villuendas P, Ortuño MA, Lledûs A, Urriolabeitia EP. Chem Eur J, 2015, 21: 8626–8636

    Article  CAS  Google Scholar 

  125. Ajitha MJ, Huang KW, Kwak J, Kim HJ, Chang S, Jung Y. Dalton Trans, 2016, 45: 7980–7985

    Article  CAS  Google Scholar 

  126. Cheng GJ, Yang YF, Liu P, Chen P, Sun TY, Li G, Zhang X, Houk KN, Yu JQ, Wu YD. J Am Chem Soc, 2014, 136: 894–897

    Article  CAS  Google Scholar 

  127. Haines BE, Musaev DG. ACS Catal, 2015, 5: 830–840

    Article  CAS  Google Scholar 

  128. Dang Y, Qu S, Nelson JW, Pham HD, Wang ZX, Wang X. J Am Chem Soc, 2015, 137: 2006–2014

    Article  CAS  Google Scholar 

  129. O’Reilly ME, Fu R, Nielsen RJ, Sabat M, Goddard WA, Gunnoe TB. J Am Chem Soc, 2014, 136: 14690–14693

    Article  CAS  Google Scholar 

  130. Wu W, Liu Y, Bi S. Org Biomol Chem, 2015, 13: 8251–8260

    Article  CAS  Google Scholar 

  131. Yang Y, Liu P. ACS Catal, 2015, 5: 2944–2951

    Article  CAS  Google Scholar 

  132. Duarte FJS, Poli G, Calhorda MJ. ACS Catal, 2016, 6: 1772–1784

    Article  CAS  Google Scholar 

  133. Thawani A, Rajeev R, Sunoj RB. Chem Eur J, 2013, 19: 4069–4077

    Article  CAS  Google Scholar 

  134. Zhang M, Huang G. Dalton Trans, 2016, 45: 3552–3557

    Article  CAS  Google Scholar 

  135. Huang G, Liu P. ACS Catal, 2016, 6: 809–820

    Article  CAS  Google Scholar 

  136. Lee SH, Gorelsky SI, Nikonov GI. Organometallics, 2013, 32: 6599–6604

    Article  CAS  Google Scholar 

  137. Luo X, Bai R, Liu S, Shan C, Chen C, Lan Y. J Org Chem, 2016, 81: 2320–2326

    Article  CAS  Google Scholar 

  138. Kantchev EAB, Pangestu SR, Zhou F, Sullivan MB, Su HB. Chem Eur J, 2014, 20: 15625–15634

    Article  CAS  Google Scholar 

  139. Liu YY, Geng ZY, Wang YC, Liu JL, Hou XF. Comput Theor Chem, 2013, 1015: 52–63

    Article  CAS  Google Scholar 

  140. Wang M, Zhang X, Chen Z, Tang YH, Lei M. Sci China Chem, 2014, 57: 1264–1275

    Article  CAS  Google Scholar 

  141. Thenraj M, Samuelson AG. Organometallics, 2013, 32: 7141–7152

    Article  CAS  Google Scholar 

  142. Campos J, Ortega-Moreno L, Conejero S, Peloso R. López-Serrano J, Maya C, Carmona E. Chem Eur J, 2015, 21: 8883–8896

    Article  CAS  Google Scholar 

  143. Miscione GP, Bottoni A. Organometallics, 2014, 33: 4173–4182

    Article  CAS  Google Scholar 

  144. Song C, Dang Y, Tao Y, Wang ZX. Organometallics, 2015, 34: 5233–5244

    Article  CAS  Google Scholar 

  145. Yu H, Fu Y. Chem Eur J, 2012, 18: 16765–16773

    Article  CAS  Google Scholar 

  146. Jiang YY, Li Z, Shi J. Organometallics, 2012, 31: 4356–4366

    Article  CAS  Google Scholar 

  147. Li Z, Liu L. Chin. Catal, 2015, 36: 3–14

    Article  CAS  Google Scholar 

  148. Yang Z, Yu H, Fu Y. Chem Eur J, 2013, 19: 12093–12103

    Article  CAS  Google Scholar 

  149. Li J, Zhang D, Sun H, Li X. Org Biomol Chem, 2014, 12: 1897–1907

    Article  CAS  Google Scholar 

  150. Meng Q, Wang F, Li M. J Mol Model, 2013, 19: 2225–2234

    Article  CAS  Google Scholar 

  151. Xu X, Jia J, Sun H, Liu Y, Xu W, Shi Y, Zhang D, Li X. Dalton Trans, 2013, 42: 3417–3428

    Article  CAS  Google Scholar 

  152. Pitts AL, Hall MB. Organometallics, 2015, 34: 3129–3140

    Article  CAS  Google Scholar 

  153. Bellows SM, Cundari TR, Jones WD. Organometallics, 2015, 34: 4032–4038

    Article  CAS  Google Scholar 

  154. Sun Y, Tang H, Chen K, Hu L, Yao J, Shaik S, Chen H. J Am Chem Soc, 2016, 138: 3715–3730

    Article  CAS  Google Scholar 

  155. Huang G. Org Lett, 2015, 17: 1994–1997

    Article  CAS  Google Scholar 

  156. Pasha FA, Bendjeriou-Sedjerari A, Huang KW, Basset JM. Organometallics, 2014, 33: 3320–3327

    Article  CAS  Google Scholar 

  157. McKay D, Riddlestone IM, Macgregor SA, Mahon MF, Whittlesey MK. ACS Catal, 2015, 5: 776–787

    Article  CAS  Google Scholar 

  158. Yang Y, Zhang Q, Shi J, Fu Y. Acta Chim Sinica, 2016, 74: 422–428

    Article  CAS  Google Scholar 

  159. Mathew J, Koga N, Suresh CH. Organometallics, 2008, 27: 4666–4670

    Article  CAS  Google Scholar 

  160. Boultadakis-Arapinis M, Gandon V, Prost E, Micouin L, Lecourt T. Adv Synth Catal, 2014, 356: 2493–2505

    Article  CAS  Google Scholar 

  161. Liu Y, Zhang D, Zhou J, Liu C. J Phys Chem A, 2010, 114: 6164–6170

    Article  CAS  Google Scholar 

  162. Varela-Álvarez A, Musaev DG. Chem Sci, 2013, 4: 3758–3764

    Article  CAS  Google Scholar 

  163. Liu H, Duan JX, Qu D, Guo LP, Xie ZZ. Organometallics, 2016, 35: 2003–2009

    Article  CAS  Google Scholar 

  164. Batiste L, Chen P. J Am Chem Soc, 2014, 136: 9296–9307

    Article  CAS  Google Scholar 

  165. Mamidipalli P, Yun SY, Wang KP, Zhou T, Xia Y, Lee D. Chem Sci, 2014, 5: 2362–2367

    Article  CAS  Google Scholar 

  166. Guo Z, Guan X, Huang JS, Tsui WM, Lin Z, Che CM. Chem Eur J, 2013, 19: 11320–11331

    Article  CAS  Google Scholar 

  167. Manca G, Gallo E, Intrieri D, Mealli C. ACS Catal, 2014, 4: 823–832

    Article  CAS  Google Scholar 

  168. Song RJ, Liu Y, Xie YX, Li JH. Synthesis, 2015, 47: 1195–1209

    Article  CAS  Google Scholar 

  169. Wendlandt AE, Suess AM, Stahl SS. Angew Chem Int Ed, 2011, 50: 11062–11087

    Article  CAS  Google Scholar 

  170. Lei J, Huang J, Zhu Q. Org Biomol Chem, 2016, 14: 2593–2602

    Article  CAS  Google Scholar 

  171. Zhang B, Studer A. Chem Soc Rev, 2015, 44: 3505–3521

    Article  CAS  Google Scholar 

  172. Guo XK, Zhang LB, Wei D, Niu JL. Chem Sci, 2015, 6: 7059–7071

    Article  CAS  Google Scholar 

  173. Suess AM, Ertem MZ, Cramer CJ, Stahl SS. J Am Chem Soc, 2013, 135: 9797–9804

    Article  CAS  Google Scholar 

  174. Jones GO, Liu P, Houk KN, Buchwald SL. J Am Chem Soc, 2010, 132: 6205–6213

    Article  CAS  Google Scholar 

  175. Ullman AM, Nocera DG. J Am Chem Soc, 2013, 135: 15053–15061

    Article  CAS  Google Scholar 

  176. Zhang Q, Zhang ZQ, Fu Y, Yu HZ. ACS Catal, 2016, 6: 798–808

    Article  CAS  Google Scholar 

  177. Wei J, Jiang J, Xiao X, Lin D, Deng Y, Ke Z, Jiang H, Zeng W. J Org Chem, 2016, 81: 946–955

    Article  CAS  Google Scholar 

  178. Guihaumé J, Halbert S, Eisenstein O, Perutz RN. Organometallics, 2012, 31: 1300–1314

    Article  CAS  Google Scholar 

  179. Xiao LJ, Fu XN, Zhou MJ, Xie JH, Wang LX, Xu XF, Zhou QL. J Am Chem Soc, 2016, 138: 2957–2960

    Article  CAS  Google Scholar 

  180. Nett AJ, Zhao W, Zimmerman PM, Montgomery J. J Am Chem Soc, 2015, 137: 7636–7639

    Article  CAS  Google Scholar 

  181. Fallon BJ, Derat E, Amatore M, Aubert C, Chemla F, Ferreira F, Perez-Luna A, Petit M. Org Lett, 2016, 18: 2292–2295

    Article  CAS  Google Scholar 

  182. Hamzaoui B, Pelletier JDA, Abou-Hamad E, Chen Y. El Eter M, Chermak E, Cavallo L, Basset JM. Chem Eur J, 2016, 22: 3000–3008

    Article  CAS  Google Scholar 

  183. Sun X, Sun X, Geng C, Zhao H, Li J. J Phys Chem A, 2014, 118: 7146–7158

    Article  CAS  Google Scholar 

  184. Tang H, Guan J, Liu H, Huang X. Dalton Trans, 2013, 42: 10260–10270

    Article  CAS  Google Scholar 

  185. Ji L, Franke A, Brindell M, Oszajca M, Zahl A, van Eldik R. Chem Eur J, 2014, 20: 14437–14450

    Article  CAS  Google Scholar 

  186. Singh KK, Tiwari MK, Ghosh M, Panda C, Weitz A, Hendrich MP, Dhar BB, Vanka K. Sen Gupta S. Inorg Chem, 2015, 54: 1535–1542

    Article  CAS  Google Scholar 

  187. Mai BK, Kim Y. Inorg Chem, 2016, 55: 3844–3852

    Article  CAS  Google Scholar 

  188. Liu W, Groves JT. Acc Chem Res, 2015, 48: 1727–1735

    Article  CAS  Google Scholar 

  189. Dhuri SN, Cho KB, Lee YM, Shin SY, Kim JH, Mandal D, Shaik S, Nam W. J Am Chem Soc, 2015, 137: 8623–8632

    Article  CAS  Google Scholar 

  190. Dietl N, Zhang X, van der Linde C, Beyer MK, Schlangen M, Schwarz H. Chem Eur J, 2013, 19: 3017–3028

    Article  CAS  Google Scholar 

  191. Wang ZC, Yin S, Bernstein ER. J Phys Chem A, 2013, 117: 2294–2301

    Article  CAS  Google Scholar 

  192. Chen XX, Xie B, Wang YC. Comput Theor Chem, 2015: 1054: 63–70

    Article  CAS  Google Scholar 

  193. Rezabal E, Ruipérez F, Ugalde JM. Phys Chem Chem Phys, 2013, 15: 1148–1153

    Article  CAS  Google Scholar 

  194. Rijs NJ, Weiske T, Schlangen M, Schwarz H. Chem Phys Lett, 2014, 608: 408–424

    Article  CAS  Google Scholar 

  195. Rijs NJ, González-Navarrete P, Schlangen M, Schwarz H. J Am Chem Soc, 2016, 138: 3125–3135

    Article  CAS  Google Scholar 

  196. Cho KB, Kang H, Woo J, Park YJ, Seo MS, Cho J, Nam W. Inorg Chem, 2014, 53: 645–652

    Article  CAS  Google Scholar 

  197. Sun X, Sun X, Geng C, Zhao H, Li J. J Phys Chem A, 2014, 118: 7146–7158

    Article  CAS  Google Scholar 

  198. Li ZF, Fan Y. De Yonker NJ, Zhang X, Su CY, Xu H, Xu X, Zhao C. J Org Chem, 2012, 77: 6076–6086

    Article  CAS  Google Scholar 

  199. Jin L, Wu Y, Zhao X. Organometallics, 2012, 31: 3065–3073

    Article  CAS  Google Scholar 

  200. Li ZF, Li HX, Yang XP, Liu XW, Zuo GF, Zhao C. RSC Adv, 2015, 5: 31954–31964

    Article  CAS  Google Scholar 

  201. Wang Y, Liao W, Huang G, Xia Y, Yu ZX. J Org Chem, 2014, 79: 5684–5696

    Article  CAS  Google Scholar 

  202. Noyori R, Yamakawa M, Hashiguchi S. J Org Chem, 2001, 66: 7931–7944

    Article  CAS  Google Scholar 

  203. Li H, Wang X, Huang F, Lu G, Jiang J, Wang ZX. Organometallics, 2011, 30: 5233–5247

    Article  CAS  Google Scholar 

  204. Li H, Wang X, Wen M, Wang ZX. Eur. Inorg Chem, 2012, 5011–5020

    Google Scholar 

  205. Li H, Wen M, Wang ZX. Inorg Chem, 2012, 51: 5716–5727

    Article  CAS  Google Scholar 

  206. Li H, Hall MB. J Am Chem Soc, 2014, 136: 383–395

    Article  CAS  Google Scholar 

  207. Lei M, Pan Y, Ma X. Eur. Inorg Chem, 2015: 794–803

    Google Scholar 

  208. Jiang YY, Xu ZY, Yu HZ, Fu Y. Sci China Chem, 2016, 59: 724–729

    Article  CAS  Google Scholar 

  209. Zhou L, Tang S, Qi X, Lin C, Liu K, Liu C, Lan Y, Lei A. Org Lett, 2014, 16: 3404–3407

    Article  CAS  Google Scholar 

  210. Liu D, Li Y, Qi X, Liu C, Lan Y, Lei A. Org Lett, 2015, 17: 998–1001

    Article  CAS  Google Scholar 

  211. Zhou L, Yi H, Zhu L, Qi X, Jiang H, Liu C, Feng Y, Lan Y, Lei A. Sci Rep, 2015, 5: 15934

    Article  CAS  Google Scholar 

  212. Binstead RA, Moyer BA, Samuels GJ, Meyer TJ. J Am Chem Soc, 1981, 103: 2897–2899

    Article  CAS  Google Scholar 

  213. Huynh MHV, Meyer TJ. Chem Rev, 2007, 107: 5004–5064

    Article  CAS  Google Scholar 

  214. Hammes-Schiffer S. Chem Rev, 2010, 110: 6937–6938

    Article  CAS  Google Scholar 

  215. Weinberg DR, Gagliardi CJ, Hull JF, Murphy CF, Kent CA, Westlake BC, Paul A, Ess DH. McCafferty DG, Meyer TJ. Chem Rev, 2012, 112: 4016–4093

    Article  CAS  Google Scholar 

  216. Tishchenko O, Truhlar DG, Ceulemans A, Nguyen MT. J Am Chem Soc, 2008, 130: 7000–7010

    Article  CAS  Google Scholar 

  217. Skone JH, Soudackov AV, Hammes-Schiffer S. J Am Chem Soc, 2006, 128: 16655–16663

    Article  CAS  Google Scholar 

  218. Mayer JM, Hrovat DA, Thomas JL, Borden WT. J Am Chem Soc, 2002, 124: 11142–11147

    Article  CAS  Google Scholar 

  219. Lingwood M, Hammond JR, Hrovat DA, Mayer JM, Borden WT. J Chem Theory Comput, 2006, 2: 740–745

    Article  CAS  Google Scholar 

  220. Usharani D, Lacy DC, Borovik AS, Shaik S. J Am Chem Soc, 2013, 135: 17090–17104

    Article  CAS  Google Scholar 

  221. Lai W, Li C, Chen H, Shaik S. Angew Chem Int Ed, 2012, 51: 5556–5578

    Article  CAS  Google Scholar 

  222. Li C, Danovich D, Shaik S. Chem Sci, 2012, 3: 1903–1918

    Article  CAS  Google Scholar 

  223. Su P, Song L, Wu W, Hiberty PC, Shaik S. J Am Chem Soc, 2004, 126: 13539–13549

    Article  CAS  Google Scholar 

  224. Cembran A, Provorse MR, Wang C, Wu W, Gao J. J Chem Theory Comput, 2012, 8: 4347–4358

    Article  CAS  Google Scholar 

  225. Shang R, Yang ZW, Wang Y, Zhang SL, Liu L. J Am Chem Soc, 2010, 132: 14391–14393

    Article  CAS  Google Scholar 

  226. Li Z, Zhang SL, Fu Y, Guo QX, Liu L. J Am Chem Soc 2009, 131: 8815–8823

    Article  CAS  Google Scholar 

  227. Becke AD. J Chem Phys, 1993, 98: 5648–5652

    Article  CAS  Google Scholar 

  228. Lee C, Yang W, Parr RG. Phys Rev B, 1988, 37: 785–789

    Article  CAS  Google Scholar 

  229. Zhao Y, Truhlar DG. Acc Chem Res, 2008, 41: 157–167

    Article  CAS  Google Scholar 

  230. Chai JD. Phys Chem Chem Phys, 2008, 10: 6615–6620

    Article  CAS  Google Scholar 

  231. Jiang Y, Yu H, Fu Y, Liu L. Sci China Chem, 2015, 58: 673–683

    Article  CAS  Google Scholar 

  232. Perdew JP, Burke K, Ernzerhof M. Phys Rev Lett, 1996, 77: 3865–3868

    Article  CAS  Google Scholar 

  233. Perdew JP, Yue W. Phys Rev B, 1986, 33: 8800–8802

    Article  Google Scholar 

  234. Becke AD. Phys Rev A, 1988, 38: 3098–3100

    Article  CAS  Google Scholar 

  235. Perdew JP. Phys Rev B, 1986, 33: 8822–8824

    Article  Google Scholar 

  236. Grimme S, Antony J, Ehrlich S, Krieg H. J Chem Phys, 2010, 132: 154104

    Article  CAS  Google Scholar 

  237. Grafenstein J, Izotov D, Cremer D. J Chem Phys, 2007, 127: 214103

    Google Scholar 

  238. Johnson ER, Becke AD, Sherrill CD. Di Labio GA. J Chem Phys, 2009, 131: 034111

    Article  CAS  Google Scholar 

  239. Ribeiro RF, Marenich AV, Cramer CJ, Truhlar DG. J Phys Chem B, 2011, 115: 14556–14562

    Article  CAS  Google Scholar 

  240. Tomasi J, Mennucci B, Cammi R. Chem Rev, 2005, 105: 2999–3093

    Article  CAS  Google Scholar 

  241. Fu Y, Shen K, Liu L, Guo QX. J Am Chem Soc, 2007, 129: 13510–13519

    Article  CAS  Google Scholar 

  242. Marenich AV, Cramer CJ, Truhlar DG. J Phys Chem B, 2009, 113: 6378–6396

    Article  CAS  Google Scholar 

  243. Barone V, Cossi M. J Phys Chem A, 1998, 102: 1995–2001

    Article  CAS  Google Scholar 

  244. Cossi M, Rega N, Scalmani G, Barone V. J Comp Chem, 2003, 24: 669–681

    Article  CAS  Google Scholar 

  245. Klamt A, Schüürmann G. J Chem Soc, Perkin Trans, 1993, 2: 799–805

    Article  Google Scholar 

  246. Hay PJ, Wadt WR. J Chem Phys, 1985, 82: 270–283

    Article  CAS  Google Scholar 

  247. Hay PJ, Wadt WR. J Chem Phys, 1985, 82: 299–310

    Article  CAS  Google Scholar 

  248. Ehlers AW, Biihme M, Dapprich S, Gobbi A, Hijllwarth A, Jonas V, Kiihler KF, Stegmann R, Veldkamp A, Frenking G. Chem Phys Lett, 1993, 208: 111–114

    Article  CAS  Google Scholar 

  249. Andrae D, Haussermann U, Dolg M, Stoll H, Preuss H. Theor Chim Acta, 1990, 77: 123–141

    Article  CAS  Google Scholar 

  250. Dolg M, Wedig U, Stoll H, Preuss H. J Chem Phys, 1987, 86: 866–872

    Article  CAS  Google Scholar 

  251. Godbout N, Salahub DR, Andzelm J, Wimmer E. Can. Chem, 1992, 70: 560–571

    Article  CAS  Google Scholar 

  252. Sosa C, Lee C. J Phys Chem, 1992, 96: 6630–6636

    Article  CAS  Google Scholar 

  253. Schafer A, Huber C, Ahlrichs R. J Chem Phys, 1994, 100, 5829–5835

    Article  Google Scholar 

  254. Schafer A, Horn H, Ahlrichs R. J Chem Phys, 1992, 97: 2571–2577

    Article  Google Scholar 

  255. Peverati R, Truhlar DG. J Phys Chem Lett, 2011, 2: 2810–2817

    Article  CAS  Google Scholar 

  256. Weigend F, Ahlrichs R. Phys Chem Chem Phys, 2005, 7: 3297–3305

    Article  CAS  Google Scholar 

  257. Weigend F. Phys Chem Chem Phys, 2006, 8: 1057–1065

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, 273165, China

    Yuan-Ye Jiang, Xiaoping Man & Siwei Bi

Authors
  1. Yuan-Ye Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xiaoping Man
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Siwei Bi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Yuan-Ye Jiang or Siwei Bi.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jiang, YY., Man, X. & Bi, S. Advances in theoretical study on transition-metal-catalyzed C−H activation. Sci. China Chem. 59, 1448–1466 (2016). https://doi.org/10.1007/s11426-016-0330-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-016-0330-3

Keywords

Search

Navigation