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Sulfur Ylides in Organic Synthesis and Transition Metal Catalysis

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Modern Ylide Chemistry

Part of the book series: Structure and Bonding ((STRUCTURE,volume 177))

Abstract

Sulfur-based ylides have long been used for a number of classical transformations, in particular for the synthesis of small ring systems and various rearrangement reactions. By combining the unorthodox reactivity of such ylides with the strength and flexibility of transition-metal catalysis, a growing number of groups have in recent years looked to expand their application in organic synthesis. This chapter aims to summarise recent developments in transition-metal-catalysed sulfonium/sulfoxonium ylide reactions as well as to offer historical perspective. In overviewing the successes in this area, the authors hope to encourage others into this growing field.

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References

  1. Bravo P, Fronza G, Ticozzi C, Gaudiano G (1974) J Organomet Chem 74:143–154

    Article  CAS  Google Scholar 

  2. Weber L (1983) Angew Chem Int Ed 22:516–528

    Article  Google Scholar 

  3. Koezuka H, Matsubayashi G, Tanaka T (1974) Inorg Chem 13:443–446

    CAS  Google Scholar 

  4. Sabounchei SJ, Akhlaghi Bagherjeri F, Hosseinzadeh M, Boskovic C, Gable RW (2014) C R Chim 17:1257–1263

    Article  CAS  Google Scholar 

  5. Sabounchei SJ, Akhlaghi Bagherjeri F, Boskovic C, Gable RW (2013) J Mol Struct 1046:39–43

    Article  CAS  Google Scholar 

  6. Sabounchei SJ, Akhlaghi Bagherjeri F, Mozafari Z, Boskovic C, Gable RW, Karamian R, Asadbegy M (2013) Dalton Trans 42:2520–2529

    Article  CAS  PubMed  Google Scholar 

  7. Kawafune I, Matsubayashi G-E (1983) Inorg Chim Acta 70:1–5

    Article  CAS  Google Scholar 

  8. Sabounchei SJ, Hashemi A (2014) Inorg Chem Commun 47:123–127

    Article  CAS  Google Scholar 

  9. Sabounchei SJ, Yousefi A, Ahmadianpoor M, Hashemi A, Bayat M, Sedghi A, Akhlaghi Bagherjeri F, Gable RW (2016) Polyhedron 117:273–282

    Article  CAS  Google Scholar 

  10. Sabounchei SJ, Hashemi A, Sedghi A, Bayat M, Akhlaghi Bagherjeri F, Gable RW (2017) J Mol Struct 1135:174–185

    Article  CAS  Google Scholar 

  11. Sabounchei SJ, Ahmadianpoor M, Yousefi A, Hashemi A, Bayat M, Sedghi A, Akhlaghi Bagherjeri F, Gable RW (2016) RSC Adv 6:28308–28315

    Article  CAS  Google Scholar 

  12. Clagett M, Gooch A, Graham P, Holy N, Mains B, Strunk J (1976) J Org Chem 41:4033–4035

    Article  CAS  Google Scholar 

  13. Lu L-Q, Chen J-R, Xiao W-J (2012) Acc Chem Res 45:1278–1293

    Article  CAS  PubMed  Google Scholar 

  14. Chen J-R, Dong W-R, Candy M, Pan F-F, Jörres M, Bolm C (2012) J Am Chem Soc 134:6924–6927

    Article  CAS  PubMed  Google Scholar 

  15. Hatcher JM, Coltart DM (2010) J Am Chem Soc 132:4546–4547

    Article  CAS  PubMed  Google Scholar 

  16. Li T-R, Tan F, Lu L-Q, Wei Y, Wang Y-N, Liu Y-Y, Yang Q-Q, Chen J-R, Shi D-Q, Xiao W-J (2014) Nat Commun 5:5500

    Article  CAS  PubMed  Google Scholar 

  17. Wang Q, Qi X, Lu L-Q, Li T-R, Yuan Z-G, Zhang K, Li B-J, Lan Y, Xiao W-J (2016) Angew Chem Int Ed 55:2840–2844

    Article  CAS  Google Scholar 

  18. Plietker B (2008) Iron catalysis in organic chemistry: reactions and applications. Wiley-VCH, Weinheim

    Google Scholar 

  19. Wang Q, Li T-R, Lu L-Q, Li M-M, Zheng K, Xiao W-J (2016) J Am Chem Soc 138:8360–8363

    Article  CAS  PubMed  Google Scholar 

  20. Detz RJ (2009) Triazole-based P,N ligands: discovery of an enantioselective copper catalysed propargylic amination reaction. PhD thesis

    Google Scholar 

  21. Nishibayashi Y, Uemura S (2008) Metal vinylidenes and allenylidenes in catalysis. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, pp 217–250

    Book  Google Scholar 

  22. Xu X, Doyle MP (2014) Acc Chem Res 47:1396–1405

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Deng Y, Massey LA, Zavalij PY, Doyle MP (2017) Angew Chem Int Ed 56:7479–7483

    CAS  Google Scholar 

  24. Kramer S, Skrydstrup T (2012) Angew Chem Int Ed 51:4681–4684

    Article  CAS  Google Scholar 

  25. Huang X, Goddard R, Maulide N (2010) Angew Chem Int Ed 49:8979–8983

    Article  CAS  Google Scholar 

  26. Huang X, Peng B, Luparia M, Gomes LFR, Veiros LF, Maulide N (2012) Angew Chem Int Ed 51:8886–8890

    Article  CAS  Google Scholar 

  27. Klimczyk S, Huang X, Kählig H, Veiros LF, Maulide N (2015) J Org Chem 80:5719–5729

    Article  CAS  PubMed  Google Scholar 

  28. Klimczyk S, Misale A, Huang X, Maulide N (2015) Angew Chem Int Ed 54:10365–10369

    Article  CAS  Google Scholar 

  29. Sabbatani J, Huang X, Veiros LF, Maulide N (2014) Chem Eur J 20:10636–10639

    Article  CAS  PubMed  Google Scholar 

  30. Unthank MG, Hussain N, Aggarwal VK (2006) Angew Chem Int Ed 45:7066–7069

    Article  CAS  Google Scholar 

  31. Yar M, McGarrigle EM, Aggarwal VK (2008) Angew Chem Int Ed 47:3784–3786

    Article  CAS  Google Scholar 

  32. Unthank MG, Tavassoli B, Aggarwal VK (2008) Org Lett 10:1501–1504

    Article  CAS  PubMed  Google Scholar 

  33. Matlock JV, Svejstrup TD, Songara P, Overington S, McGarrigle EM, Aggarwal VK (2015) Org Lett 17:5044–5047

    Article  CAS  PubMed  Google Scholar 

  34. Klose I, Misale A, Maulide N (2016) J Org Chem 81:7201–7210

    Article  CAS  PubMed  Google Scholar 

  35. Huang X, Goddard R, Maulide N (2013) Chem Commun 49:4292–4294

    Article  CAS  Google Scholar 

  36. Liu Y-Y, Yang X-H, Huang X-C, Wei W-T, Song R-J, Li J-H (2013) J Org Chem 78:10421–10426

    Article  CAS  PubMed  Google Scholar 

  37. Wang L, He W, Yu Z (2013) Chem Soc Rev 42:599–621

    Article  CAS  PubMed  Google Scholar 

  38. Srogl J, Allred GD, Liebeskind LS (1997) J Am Chem Soc 119:12376–12377

    Article  CAS  Google Scholar 

  39. Hooper JF, Chaplin AB, González-Rodríguez C, Thompson AL, Weller AS, Willis MC (2012) J Am Chem Soc 134:2906–2909

    Article  CAS  PubMed  Google Scholar 

  40. Prier CK, Rankic DA, MacMillan DWC (2013) Chem Rev 113:5322–5363

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  41. Shaw MH, Twilton J, MacMillan DWC (2016) J Org Chem 81:6898–6926

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. Xia X-D, Lu L-Q, Liu W-Q, Chen D-Z, Zheng Y-H, Wu L-Z, Xiao W-J (2016) Chem Eur J 22:8432–8437

    Article  CAS  PubMed  Google Scholar 

  43. Trost BM (1966) J Am Chem Soc 88:1587–1588

    Article  CAS  Google Scholar 

  44. Burtoloso ACB, Dias RMP, Leonarczyk IA (2013) Eur J Org Chem 2013:5005–5016

    Google Scholar 

  45. Zhang Z, Wang J (2008) Tetrahedron 64:6577–6605

    Article  CAS  Google Scholar 

  46. Deng Y, Qiu H, Srinivas HD, Doyle MP (2016) Curr Org Chem 20:61–81

    Article  CAS  Google Scholar 

  47. Doyle MP, Duffy R, Ratnikov M, Zhou L (2010) Chem Rev 110:704–724

    Article  CAS  PubMed  Google Scholar 

  48. Peña-López M, Beller M (2017) Angew Chem Int Ed 56:46–48

    Article  CAS  Google Scholar 

  49. Moody CJ (2007) Angew Chem Int Ed 46:9148–9150

    Article  CAS  Google Scholar 

  50. Cohen T, Herman G, Chapman TM, Kuhn D (1974) J Am Chem Soc 96:5627–5628

    Article  CAS  Google Scholar 

  51. Cimetière B, Julia M (1991) Synlett 1991:271–272

    Article  Google Scholar 

  52. Müller P, Fernandez D, Nury P, Rossier J-C (1999) Helv Chim Acta 82:935–945

    Article  Google Scholar 

  53. Duan Y, Lin J-H, Xiao J-C, Gu Y-C (2016) Org Lett 18:2471–2474

    Article  CAS  PubMed  Google Scholar 

  54. Duan Y, Lin J-H, Xiao J-C, Gu Y-C (2017) Chem Commun 53:3870–3873

    Article  CAS  Google Scholar 

  55. Baldwin JE, Adlington RM, Godfrey CRA, Gollins DW, Vaughan JG (1993) J Chem Soc Chem Commun:1434–1435

    Google Scholar 

  56. Mangion IK, Nwamba IK, Shevlin M, Huffman MA (2009) Org Lett 11:3566–3569

    Article  CAS  PubMed  Google Scholar 

  57. Mangion IK, Weisel M (2010) Tetrahedron Lett 51:5490–5492

    Article  CAS  Google Scholar 

  58. Molinaro C, Bulger PG, Lee EE, Kosjek B, Lau S, Gauvreau D, Howard ME, Wallace DJ, O’Shea PD (2012) J Org Chem 77:2299–2309

    Article  CAS  PubMed  Google Scholar 

  59. Mangion IK, Ruck RT, Rivera N, Huffman MA, Shevlin M (2011) Org Lett 13:5480–5483

    Article  CAS  PubMed  Google Scholar 

  60. Phelps AM, Chan VS, Napolitano JG, Krabbe SW, Schomaker JM, Shekhar S (2016) J Org Chem 81:4158–4169

    Article  CAS  PubMed  Google Scholar 

  61. Vaitla J, Bayer A, Hopmann KH (2017) Angew Chem Int Ed 56:4277–4281

    Article  CAS  Google Scholar 

  62. Gandelman M, Rybtchinski B, Ashkenazi N, Gauvin RM, Milstein D (2001) J Am Chem Soc 123:5372–5373

    Article  CAS  PubMed  Google Scholar 

  63. Gandelman M, Naing KM, Rybtchinski B, Poverenov E, Ben-David Y, Ashkenazi N, Gauvin RM, Milstein D (2005) J Am Chem Soc 127:15265–15272

    Article  CAS  PubMed  Google Scholar 

  64. Suarez AIO, del Río MP, Remerie K, Reek JNH, de Bruin B (2012) ACS Catal 2:2046–2059

    Article  CAS  Google Scholar 

  65. Padwa A, Hornbuckle SF (1991) Chem Rev 91:263–309

    Article  CAS  Google Scholar 

  66. Diekmann J (1965) J Org Chem 30:2272–2275

    Article  CAS  Google Scholar 

  67. Ando W, Yagihara T, Tozune S, Nakaido S, Migita T (1969) Tetrahedron Lett 10:1979–1982

    Article  Google Scholar 

  68. Ando W, Yagihara T, Tozune S, Imai I, Suzuki J, Toyama T, Nakaido S, Migita T (1972) J Org Chem 37:1721–1727

    Article  CAS  Google Scholar 

  69. Gillespie RJ, Porter AEA, Willmott WE (1978) J Chem Soc Chem Commun:83–84

    Google Scholar 

  70. Zhang Y, Wang J (2010) Coord Chem Rev 254:941–953

    Article  CAS  Google Scholar 

  71. Jones AC, May JA, Sarpong R, Stoltz BM (2014) Angew Chem Int Ed 53:2556–2591

    Article  CAS  Google Scholar 

  72. Sheng Z, Zhang Z, Chu C, Zhang Y, Wang J (2016) Tetrahedron 73:4011–4022

    Article  CAS  Google Scholar 

  73. Kirmse W, Kapps M (1968) Chem Ber 101:994–1003

    Article  CAS  Google Scholar 

  74. Doyle MP, Griffin JH, Chinn MS, Van Leusen D (1984) J Org Chem 49:1917–1925

    Article  CAS  Google Scholar 

  75. Fukuda T, Katsuki T (1997) Tetrahedron Lett 38:3435–3438

    Article  CAS  Google Scholar 

  76. Davies PW, Albrecht SJC, Assanelli G (2009) Org Biomol Chem 7:1276–1279

    Article  CAS  PubMed  Google Scholar 

  77. Greenman KL, Carter DS, Van Vranken DL (2001) Tetrahedron 57:5219–5225

    Article  CAS  Google Scholar 

  78. Zhou C-Y, Yu W-Y, Chan PWH, Che C-M (2004) J Org Chem 69:7072–7082

    Article  CAS  PubMed  Google Scholar 

  79. Peng L, Zhang X, Ma M, Wang J (2007) Angew Chem Int Ed 46:1905–1908

    Article  CAS  Google Scholar 

  80. Xiao Q, Wang J-B (2007) Acta Chim Sin 65:1733–1735

    CAS  Google Scholar 

  81. Zhu S-F, Zhou Q-L (2014) Nat Sci Rev 1:580–603

    Article  CAS  Google Scholar 

  82. Carter DS, Van Vranken DL (2000) Org Lett 2:1303–1305

    Article  CAS  PubMed  Google Scholar 

  83. Prabharasuth R, Van Vranken DL (2001) J Org Chem 66:5256–5258

    Article  CAS  PubMed  Google Scholar 

  84. Xu X, Li C, Tao Z, Pan Y (2017) Green Chem 19:1245–1249

    Article  CAS  Google Scholar 

  85. Aviv I, Gross Z (2008) Chem Eur J 14:3995–4005

    Article  CAS  PubMed  Google Scholar 

  86. Holzwarth MS, Alt I, Plietker B (2012) Angew Chem Int Ed 51:5351–5354

    Article  CAS  Google Scholar 

  87. Liao M, Peng L, Wang J (2008) Org Lett 10:693–696

    Article  CAS  PubMed  Google Scholar 

  88. Li Y, Shi Y, Huang Z, Wu X, Xu P, Wang J, Zhang Y (2011) Org Lett 13:1210–1213

    Article  CAS  PubMed  Google Scholar 

  89. Nishibayashi Y, Ohe K, Uemura S (1995) J Chem Soc Chem Commun:1245–1246

    Google Scholar 

  90. Kitagaki S, Yanamoto Y, Okubo H, Nakajima M, Hashimoto S (2001) Heterocycles 54:623–628

    Article  CAS  Google Scholar 

  91. Aggarwal VK, Ferrara M, Hainz R, Spey SE (1999) Tetrahedron Lett 40:8923–8927

    Article  CAS  Google Scholar 

  92. Zhang X, Qu Z, Ma Z, Shi W, Jin X, Wang J (2002) J Org Chem 67:5621–5625

    Article  CAS  PubMed  Google Scholar 

  93. Ma M, Peng L, Li C, Zhang X, Wang J (2005) J Am Chem Soc 127:15016–15017

    Article  CAS  PubMed  Google Scholar 

  94. Trost BM, Hammen RF (1973) J Am Chem Soc 95:962–964

    Article  CAS  Google Scholar 

  95. Zhang Z, Sheng Z, Yu W, Wu G, Zhang R, Chu W-D, Zhang Y, Wang J (2017) Nat Chem 9:970–976

    Article  CAS  PubMed  Google Scholar 

  96. Li Y, Huang Z, Wu X, Xu P-F, Jin J, Zhang Y, Wang J (2012) Tetrahedron 68:5234–5240

    Article  CAS  Google Scholar 

  97. Miura T, Tanaka T, Yada A, Murakami M (2013) Chem Lett 42:1308–1310

    Article  CAS  Google Scholar 

  98. Yadagiri D, Anbarasan P (2013) Chem Eur J 19:15115–15119

    Article  CAS  PubMed  Google Scholar 

  99. Miki K, Nishino F, Ohe K, Uemura S (2002) J Am Chem Soc 124:5260–5261

    Article  CAS  PubMed  Google Scholar 

  100. Kato Y, Miki K, Nishino F, Ohe K, Uemura S (2003) Org Lett 5:2619–2621

    Article  CAS  PubMed  Google Scholar 

  101. Davies PW, Albrecht SJC (2008) Chem Commun:238–240

    Google Scholar 

  102. Davies PW, Albrecht SJC (2009) Angew Chem Int Ed 48:8372–8375

    Article  CAS  Google Scholar 

  103. Shapiro ND, Toste FD (2007) J Am Chem Soc 129:4160–4161

    Article  CAS  PubMed  Google Scholar 

  104. Li G, Zhang L (2007) Angew Chem Int Ed 46:5156–5159

    Article  CAS  Google Scholar 

  105. Santos MD, Davies PW (2014) Chem Commun 50:6001–6004

    Article  Google Scholar 

  106. Li J, Ji K, Zheng R, Nelson J, Zhang L (2014) Chem Commun 50:4130–4133

    Article  CAS  Google Scholar 

  107. Zhang H, Wang B, Yi H, Zhang Y, Wang J (2015) Org Lett 17:3322–3325

    Article  CAS  PubMed  Google Scholar 

  108. Song Z, Wu Y, Xin T, Jin C, Wen X, Sun H, Xu Q-L (2016) Chem Commun 52:6079–6082

    Article  CAS  Google Scholar 

  109. Ellis-Holder KK, Peppers BP, Kovalevsky AY, Diver ST (2006) Org Lett 8:2511–2514

    Article  CAS  PubMed  Google Scholar 

  110. Nair V, Nair SM, Mathai S, Liebscher J, Ziemer B, Narsimulu K (2004) Tetrahedron Lett 45:5759–5762

    Article  CAS  Google Scholar 

  111. Lu P, Herrmann AT, Zakarian A (2015) J Org Chem 80:7581–7589

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  112. Lin R, Cao L, West FG (2017) Org Lett 19:552–555

    Article  CAS  PubMed  Google Scholar 

  113. Qu J-P, Xu Z-H, Zhou J, Cao C-L, Sun X-L, Dai L-X, Tang Y (2009) Adv Synth Catal 351:308–312

    Article  CAS  Google Scholar 

  114. Xu X, Li C, Xiong M, Tao Z, Pan Y (2017) Chem Commun 53:6219–6222

    Article  CAS  Google Scholar 

  115. Aggarwal VK, Winn CL (2004) Acc Chem Res 37:611–620

    Article  CAS  PubMed  Google Scholar 

  116. McGarrigle EM, Aggarwal VK (2007) Enantioselective organocatalysis: reactions and experimental procedures. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, pp 357–389

    Book  Google Scholar 

  117. Aggarwal VK, Abdel-Rahman H, Jones RVH, Lee HY, Reid BD (1994) J Am Chem Soc 116:5973–5974

    Article  CAS  Google Scholar 

  118. Aggarwal VK, Abdel-Rahman H, Jones RVH, Standen MCH (1995) Tetrahedron Lett 36:1731–1732

    Article  CAS  Google Scholar 

  119. Aggarwal VK, Thompson A, Jones RVH, Standen M (1995) Tetrahedron Asymmetry 6:2557–2564

    Article  CAS  Google Scholar 

  120. Aggarwal VK, Abdel-Rahman H, Fan L, Jones RVH, Standen MCH (1996) Chem Eur J 2:1024–1030

    Article  CAS  Google Scholar 

  121. Aggarwal VK, Alonso E, Hynd G, Lydon KM, Palmer MJ, Porcelloni M, Studley JR (2001) Angew Chem Int Ed 40:1430–1433

    Article  CAS  Google Scholar 

  122. Aggarwal VK, Alonso E, Bae I, Hynd G, Lydon KM, Palmer MJ, Patel M, Porcelloni M, Richardson J, Stenson RA, Studley JR, Vasse J-L, Winn CL (2003) J Am Chem Soc 125:10926–10940

    Article  CAS  PubMed  Google Scholar 

  123. Aggarwal VK, Thompson A, Jones RVH, Standen MCH (1996) J Org Chem 61:8368–8369

    Article  CAS  Google Scholar 

  124. Aggarwal VK, Alonso E, Fang G, Ferrara M, Hynd G, Porcelloni M (2001) Angew Chem Int Ed 40:1433–1436

    Article  CAS  Google Scholar 

  125. Fulton JR, Aggarwal VK, de Vicente J (2005) Eur J Org Chem 2005:1479–1492

    Article  CAS  Google Scholar 

  126. Aggarwal VK, Smith HW, Hynd G, Jones RVH, Fieldhouse R, Spey SE (2000) J Chem Soc Perkin Trans 1:3267–3276

    Article  Google Scholar 

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Authors and Affiliations

  1. Institute of Organic Chemistry of the University of Vienna, Vienna, Austria

    Rik Oost, James D. Neuhaus, Jérémy Merad & Nuno Maulide

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  1. Rik Oost
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  2. James D. Neuhaus
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  3. Jérémy Merad
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  4. Nuno Maulide
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Correspondence to Nuno Maulide .

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Editors and Affiliations

  1. Chair of Inorganic Chemistry II , Ruhr-Universität Bochum , Bochum, Germany

    Viktoria H. Gessner

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Oost, R., Neuhaus, J.D., Merad, J., Maulide, N. (2017). Sulfur Ylides in Organic Synthesis and Transition Metal Catalysis. In: Gessner, V. (eds) Modern Ylide Chemistry. Structure and Bonding, vol 177. Springer, Cham. https://doi.org/10.1007/430_2017_14

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