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Nickel-Catalyzed Reductive Couplings

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Abstract

The Ni-catalyzed reductive coupling of alkyl/aryl with other electrophiles has evolved to be an important protocol for the construction of C–C bonds. This chapter first emphasizes the recent progress on the Ni-catalyzed alkylation, arylation/vinylation, and acylation of alkyl electrophiles. A brief overview of CO2 fixation is also addressed. The chemoselectivity between the electrophiles and the reactivity of the alkyl substrates will be detailed on the basis of different Ni-catalyzed conditions and mechanistic perspective. The asymmetric formation of C(sp3)–C(sp2) bonds arising from activated alkyl halides is next depicted followed by allylic carbonylation. Finally, the coupling of aryl halides with other C(sp2)–electrophiles is detailed at the end of this chapter.

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References

  1. Gu J, Wang X, Xue W, Gong H (2015) Org Chem Front 2:1411

    Article  CAS  Google Scholar 

  2. Everson DA, Weix DJ (2014) J Org Chem 79:4793

    Article  CAS  Google Scholar 

  3. Knappke CE, Grupe S, Gärtner D, Corpet M, Gosmini C, von Jacobi Wangelin A (2014) Chem Eur J 20:6828

    Article  CAS  Google Scholar 

  4. Weix DJ (2015) Acc Chem Res 48:1767

    Article  CAS  Google Scholar 

  5. Moragas T, Correa A, Martin R (2014) Chem Eur J 20:8242

    Article  CAS  Google Scholar 

  6. Nédélec J-Y, Périchon J, Troupel M (1997) Top Curr Chem 185:141

    Article  Google Scholar 

  7. Jana R, Pathak TP, Sigman MS (2011) Chem Rev 111:1417

    Article  CAS  Google Scholar 

  8. Thaler T, Haag B, Gavryushin A, Schober K, Hartmann E, Gschwind RM, Zipse H, Mayer P, Knochel P (2010) Nat Chem 2:125

    Article  CAS  Google Scholar 

  9. Fu GC (2008) Acc Chem Res 41:1555

    Article  CAS  Google Scholar 

  10. Netherton MR, Fu GC (2004) Adv Synth Catal 346:1525

    Article  CAS  Google Scholar 

  11. Rudolph A, Lautens M (2009) Angew Chem Int Ed 48:2656

    Article  CAS  Google Scholar 

  12. Frisch AC, Beller M (2005) Angew Chem Int Ed 44:674

    Article  CAS  Google Scholar 

  13. Hu X (2011) Chem Sci 2:1867

    Article  CAS  Google Scholar 

  14. Li Z, Liu L (2015) Chin J Catal 36:3

    Article  CAS  Google Scholar 

  15. Tasker SZ, Standley EA, Jamison TF (2014) Nature 509:299

    Article  CAS  Google Scholar 

  16. Biswas S, Weix DJ (2013) J Am Chem Soc 135:16192

    Article  CAS  Google Scholar 

  17. Breitenfeld J, Ruiz J, Wodrich MD, Hu X (2013) J Am Chem Soc 135:12004

    Article  CAS  Google Scholar 

  18. Tellis JC, Primer DN, Molander GA (2014) Science 345:433

    Article  CAS  Google Scholar 

  19. Zuo Z, Ahneman DT, Chu L, Terrett JA, Doyle AG, MacMillan DW (2014) Science 345:437

    Article  CAS  Google Scholar 

  20. Schley ND, Fu GC (2014) J Am Chem Soc 136:16588

    Article  CAS  Google Scholar 

  21. Yu X, Yang T, Wang S, Xu H, Gong H (2011) Org Lett 13:2138

    Article  CAS  Google Scholar 

  22. Xu H, Zhao C, Qian Q, Deng W, Gong H (2013) Chem Sci 4:4022

    Article  CAS  Google Scholar 

  23. Jones GD, Martin JL, McFarland C, Allen OR, Hall RE, Haley AD, Brandon RJ, Konovalova T, Desrochers PJ, Pulay P, Vicic DA (2006) J Am Chem Soc 128:13175

    Article  CAS  Google Scholar 

  24. Tsou TT, Kochi JK (1979) J Am Chem Soc 101:7547

    Article  CAS  Google Scholar 

  25. Colon I, Kelsey DR (1986) J Org Chem 51:2627

    Article  CAS  Google Scholar 

  26. Prinsell MR, Everson DA, Weix DJ (2010) Chem Commun 46:5743

    Article  CAS  Google Scholar 

  27. Goldup SM, Leigh DA, McBurney RT, McGonigal PR, Plant A (2010) Chem Sci 1:383

    Article  CAS  Google Scholar 

  28. Peng Y, Luo L, Yan C-S, Zhang J-J, Wang Y-W (2013) J Org Chem 78:10960

    Article  CAS  Google Scholar 

  29. Wada M, Murata T, Oikawa H, Oguri H (2014) Org Biomol Chem 12:298

    Article  CAS  Google Scholar 

  30. Zhang C-P, Wang H, Klein A, Biewer C, Stirnat K, Yamaguchi Y, Xu L, Gomez-Benitez V, Vicic DA (2013) J Am Chem Soc 135:8141

    Article  CAS  Google Scholar 

  31. Yu S, Dudkina Y, Wang H, Kholin K, Kadirov M, Budnikova Y, Vicic D (2015) Dalton Trans 44:19443

    Article  CAS  Google Scholar 

  32. Liang Z, Xue W, Lin K, Gong H (2014) Org Lett 16:5620

    Article  CAS  Google Scholar 

  33. Unpublished results from the author’s lab

  34. Liu JH, Yang CT, Lu XY, Zhang ZQ, Xu L, Cui M, Lu X, Xiao B, Fu Y, Liu L (2014) Chem Eur J 20:15334

    Article  CAS  Google Scholar 

  35. Durandetti M, Perichon J (2004) Synthesis 3079

  36. Dai Y, Wu F, Zang Z, You H, Gong H (2012) Chem Eur J 18:808

    Article  CAS  Google Scholar 

  37. Anka-Lufford LL, Prinsell MR, Weix DJ (2012) J Org Chem 77:9989

    Article  CAS  Google Scholar 

  38. Qian X, Auffrant A, Felouat A, Gosmini C (2011) Angew Chem Int Ed 50:10402

    Article  CAS  Google Scholar 

  39. Xue W, Xu H, Liang Z, Qian Q, Gong H (2014) Org Lett 16:4984

    Article  CAS  Google Scholar 

  40. Tollefson EJ, Erickson LW, Jarvo ER (2015) J Am Chem Soc 137:9760–9763

    Article  CAS  Google Scholar 

  41. Krasovskiy A, Duplais C, Lipshutz BH (2009) J Am Chem Soc 131:15592

    Article  CAS  Google Scholar 

  42. Czaplik WM, Mayer M, von Jacobi Wangelin A (2009) Angew Chem Int Ed 48:607

    Article  CAS  Google Scholar 

  43. Everson DA, Shrestha R, Weix DJ (2010) J Am Chem Soc 132:920

    Article  CAS  Google Scholar 

  44. Everson DA, Jones BA, Weix DJ (2012) J Am Chem Soc 134:6146

    Article  CAS  Google Scholar 

  45. Amatore M, Gosmini C (2010) Chem Eur J 16:5848

    Article  CAS  Google Scholar 

  46. Wang S, Qian Q, Gong H (2012) Org Lett 14:3352

    Article  CAS  Google Scholar 

  47. Yan CS, Peng Y, Xu XB, Wang YW (2012) Chem Eur J 18:6039

    Article  CAS  Google Scholar 

  48. Peng Y, Xu XB, Xiao J, Wang Y-W (2014) Chem Commun 50:472

    Article  CAS  Google Scholar 

  49. Lu X, Yi J, Zhang Z-Q, Dai J-J, Liu J-H, Xiao B, Fu Y, Liu L (2014) Chem Eur J 20:15339

    Article  CAS  Google Scholar 

  50. Molander GA, Traister KM, O’Neill BT (2015) J Org Chem 80:2907

    Article  CAS  Google Scholar 

  51. Li X, Feng Z, Jiang Z-X, Zhang X (2015) Org Lett 17:5570

    Article  CAS  Google Scholar 

  52. Gutierrez O, Tellis JC, Primer DN, Molander GA, Kozlowski MC (2015) J Am Chem Soc 137:4896

    Article  CAS  Google Scholar 

  53. Ackerman LK, Anka-Lufford LL, Naodovic M, Weix DJ (2015) Chem Sci 6:1115

    Article  CAS  Google Scholar 

  54. Zhao Y, Weix DJ (2013) J Am Chem Soc 136:48

    Article  CAS  Google Scholar 

  55. Yamashita Y, Tellis JC, Molander GA (2015) Proc Natl Acad Sci USA 112:12026

    Article  CAS  Google Scholar 

  56. Jouffroy M, Primer DN, Molander GA (2015) J Am Chem So 138:475

    Article  CAS  Google Scholar 

  57. Wang X, Wang S, Xue W, Gong H (2015) J Am Chem Soc 137:11562

    Article  CAS  Google Scholar 

  58. Patel NR, Kelly CB, Jouffroy M, Molander GA (2016) Org Lett 18:764

    Article  CAS  Google Scholar 

  59. Noble A, McCarver SJ, MacMillan DW (2015) J Am Chem Soc 137:624

    Article  CAS  Google Scholar 

  60. Durandetti M, Gosmini C, Périchon J (2007) Tetrahedron 63:1146

    Article  CAS  Google Scholar 

  61. Cui X, Wang S, Zhang Y, Deng W, Qian Q, Gong H (2013) Org Biomol Chem 11:3094

    Article  CAS  Google Scholar 

  62. Arendt KM, Doyle AG (2015) Angew Chem Int Ed 54:9876

    Article  CAS  Google Scholar 

  63. Konev MO, Hanna LE, Jarvo ER (2016) Angew Chem Int Ed 55: ASAP. doi:10.1002/anie.201601206

  64. Wotal AC, Weix DJ (2012) Org Lett 14:1476

    Article  CAS  Google Scholar 

  65. Wu F, Lu W, Qian Q, Ren Q, Gong H (2012) Org Lett 14:3044

    Article  CAS  Google Scholar 

  66. Yin H, Zhao C, You H, Lin K, Gong H (2012) Chem Commun 48:7034

    Article  CAS  Google Scholar 

  67. Lu W, Liang Z, Zhang Y, Wu F, Qian Q, Gong H (2013) Synthesis 45:2234

    Article  CAS  Google Scholar 

  68. Jia X, Zhang X, Qian Q, Gong H (2015) Chem Commun 51:10302

    Article  CAS  Google Scholar 

  69. Zhao C, Jia X, Wang X, Gong H (2014) J Am Chem Soc 136:17645

    Article  CAS  Google Scholar 

  70. Le CC, MacMillan DW (2015) J Am Chem Soc 137:11938

    Article  CAS  Google Scholar 

  71. Joe CL, Doyle AG (2016) Angew Chem Int Ed 55:4040

    Article  CAS  Google Scholar 

  72. Amani J, Sodagar E, Molander GA (2016) Org Lett 18:732

    Article  CAS  Google Scholar 

  73. León T, Correa A, Martin R (2013) J Am Chem Soc 135:1221

    Article  CAS  Google Scholar 

  74. Moragas T, Cornella J, Martin R (2014) J Am Chem Soc 136:17702

    Article  CAS  Google Scholar 

  75. Liu Y, Cornella J, Martin R (2014) J Am Chem Soc 136:11212

    Article  CAS  Google Scholar 

  76. Wang X, Liu Y, Martin R (2015) J Am Chem Soc 137:6476

    Article  CAS  Google Scholar 

  77. Moragas T, Gaydou M, Martin R (2016) Angew Chem Int Ed 55. doi:10.1002/anie.201600697

  78. Zhao Y, Weix DJ (2015) J Am Chem Soc 137:3237

    Article  CAS  Google Scholar 

  79. Cherney AH, Kadunce NT, Reisman SE (2013) J Am Chem Soc 135:7442

    Article  CAS  Google Scholar 

  80. Cherney AH, Reisman SE J Am Chem Soc 136:14365

  81. Kadunce NT, Reisman SE (2015) J Am Chem Soc 137:10480

    Article  CAS  Google Scholar 

  82. Zuo Z, Cong H, Li W, Choi J, Fu GC, MacMillan DWC (2016) J Am Chem Soc 138:1832

    Article  CAS  Google Scholar 

  83. Tan Z, Wan X, Zang Z, Qian Q, Deng W, Gong H (2014) Chem Commun 50:3827

    Article  CAS  Google Scholar 

  84. Liu X, Li X, Chen Y, Hu Y, Kishi Y (2012) J Am Chem Soc 134:6136

    Article  CAS  Google Scholar 

  85. Panahi F, Bahmani M, Iranpoor N (2015) Adv Synth Catal 357:1211

    Article  CAS  Google Scholar 

  86. Zhao C, Tan Z, Liang Z, Deng W, Gong H (2014) Synthesis 46:1901

    Article  CAS  Google Scholar 

  87. Caputo JA, Naodovic M, Weix DJ (2015) Synlett 26:323–326

    Article  CAS  Google Scholar 

  88. Amatore M, Gosmini C (2008) Angew Chem Int Ed 47:2089

    Article  CAS  Google Scholar 

  89. Gosmini C, Bassene-Ernst C, Durandetti M (2009) Tetrahedron 65:6141

    Article  CAS  Google Scholar 

  90. Qian Q, Zang Z, Chen Y, Lin K, Gong H (2013) Synlett 24:619

    Article  CAS  Google Scholar 

  91. Iranpoor N, Panahi F (2015) Org Lett 17:214

    Article  CAS  Google Scholar 

  92. Liao L-Y, Kong X-R, Duan X-F (2014) J Org Chem 79:777

    Article  CAS  Google Scholar 

  93. Buonomo JA, Everson DA, Weix DJ (2013) Synthesis 45:3099

    Article  CAS  Google Scholar 

  94. Ackerman LKG, Lovell MM, Weix DJ (2015) Nature 524:455

    Article  CAS  Google Scholar 

  95. Moncomble A, Le Floch P, Lledos A, Gosmini C (2012) J Org Chem 77:5056

    Article  CAS  Google Scholar 

  96. Correa A, León T, Martin R (2014) J Am Chem Soc 136:1062

    Article  CAS  Google Scholar 

  97. Wang X, Nakajima M, Martin R (2015) J Am Chem Soc 137:8924

    Article  CAS  Google Scholar 

  98. Correa A, Martin R (2014) J Am Chem Soc 136:7253

    Article  CAS  Google Scholar 

  99. Hsieh J-H, Cheng C-H (2005) Chem Commun 4554

  100. Hsieh J-C, Chen Y-C, Cheng A-Y, Tseng H-C (2012) Org Lett 14:1282

    Article  CAS  Google Scholar 

  101. Majumdar KK, Cheng CH (2000) Org Lett 2:2295

    Article  CAS  Google Scholar 

  102. Huang YC, Majumdar KK, Cheng CH (2002) J Org Chem 67:1682

    Article  CAS  Google Scholar 

  103. Hu JX, Li CY, Sheng WJ, Jia YX, Gao JR (2011) Chem Eur J 17:5234

    Article  CAS  Google Scholar 

  104. Qian Q, Zang Z, Chen Y, Tong W, Gong H (2013) Mini Rev Med Chem 13:802

    Article  CAS  Google Scholar 

  105. Lu X, Xiao B, Zhang Z, Gong T, Su W, Yi J, Fu Y, Liu L (2016) Nat Commun 7:11129

    Article  CAS  Google Scholar 

  106. Lebedev SA, Lopatina VS, Petrov ES, Beletskaya IP (1988) J Organomet Chem 344:253

    Article  CAS  Google Scholar 

  107. Liu C-C, Parthasarathy K, Cheng C-H (2010) Org Lett 15:3518

    Article  CAS  Google Scholar 

  108. Korivi RP, Cheng C-H (2006) J Org Chem 71:7079

    Article  CAS  Google Scholar 

  109. Shrestha R, Dorn SCM, Weix DJ (2013) J Am Chem Soc 135:751

    Article  CAS  Google Scholar 

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Acknowledgments

Financial support was provided by the Chinese NSF (Nos. 21172140, 21372151, and 21572127), Shanghai Municipal Education Commission for the Programs for Professor of Special Appointment (Dongfang Scholarship), Shanghai Peak Discipline Construction (N.13-A302-15-L02), and Shanghai Science and Technology Commission (14DZ2261100).

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Authors and Affiliations

  1. Department of Chemistry, Center for Supramolecular Materials and Catalysis, Shanghai University, 99 Shang-Da Road, Shanghai, 200444, China

    Xuan Wang, Yijing Dai & Hegui Gong

  2. Shanghai Key Lab of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai, 200092, China

    Hegui Gong

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  1. Xuan Wang
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  2. Yijing Dai
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  3. Hegui Gong
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Correspondence to Hegui Gong.

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This article is part of the Topical Collection “Ni- and Fe-Based Cross-Coupling Reactions”; edited by “Arkaitz Correa”.

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Wang, X., Dai, Y. & Gong, H. Nickel-Catalyzed Reductive Couplings. Top Curr Chem (Z) 374, 43 (2016). https://doi.org/10.1007/s41061-016-0042-2

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