Sulfoxonium Ylide Derived Metal Carbenoids in Organic Synthesis

Janakiram Vaitla; Annette Bayer

doi:10.1055/s-0037-1610328

Synthesis, Table of Contents

Synthesis 2019; 51(03): 612-628
DOI: 10.1055/s-0037-1610328

short review

Sulfoxonium Ylide Derived Metal Carbenoids in Organic Synthesis

Authors

Janakiram Vaitla *

Department of Chemistry, UiT – The Arctic University of Norway, N-9037 Tromsø, Norway Email: Janakiray.vaitla@uit.no Email: annette.bayer@uit.no
Annette Bayer *

Department of Chemistry, UiT – The Arctic University of Norway, N-9037 Tromsø, Norway Email: Janakiray.vaitla@uit.no Email: annette.bayer@uit.no

Abstract

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Abstract

As pioneered by Corey and Chaykovsky, sulfoxonium ylides have had widespread application in organic synthesis for more than a half century. In most of the reactions, sulfoxonium ylides were used to react with electrophiles. Under suitable reaction conditions these ylides can generate metal carbenoids and react with nucleophiles. By combining the typical reactivity of sulfoxonium ylides with transition-metal catalysis, a growing number of investigations have expanded their application in organic synthesis. This review provides an update on the preparation of sulfoxonium ylides and their applications in carbenoid transfer reactions.

1 Introduction

2 Preparation of Sulfoxonium Ylides

3 Investigation for Carbenoid Formation from Sulfoxonium Ylide

4 X–H (X = N, O, S, C) Functionalization Reactions

5 Polymerizaton of Carbenoids Generated from Sulfoxonium Ylides

6 Conclusion and Perspective

Key words

sulfur ylides - metal carbenoids - transition metal catalysis - insertion reactions - C–H activation - coupling reaction - heterocycles

Full Text

References

References

1a Dötz KH. Angew. Chem. Int. Ed. Engl. 1984; 23: 587
1b Doyle MP, Forbes DC. Chem. Rev. 1998; 98: 911

2a Brookhart M, Studabaker WB. Chem. Rev. 1987; 87: 411
2b Davies HM. L, Huby NJ. S, Cantrell WR, Olive JL. J. Am. Chem. Soc. 1993; 115: 9468

3a Xu X, Doyle MP. Acc. Chem. Res. 2014; 47: 1396
3b Davies HM. L. Curr. Org. Chem. 1998; 2: 463

4 Zhu S.-F, Zhou Q.-L. Acc. Chem. Res. 2012; 45: 1365

5a Guo X, Hu W. Acc. Chem. Res. 2013; 46: 2427
5b Zhang Y, Wang J. Coord. Chem. Rev. 2010; 254: 941

6 Liu Z, Wang J. J. Org. Chem. 2013; 78: 10024

7a Ye T, McKervey MA. Chem. Rev. 1994; 94: 1091
7b Zhang Z, Wang J. Tetrahedron 2008; 64: 6577
7c Zhang Y, Wang J. Chem. Commun. 2009; 5350
7d Ford A, Miel H, Ring A, Slattery CN, Maguire AR, McKervey MA. Chem. Rev. 2015; 115: 9981

8a Moore JA, Ree DE. Org. Synth. 1961; 41: 16
8b Bio MM, Javadi G, Song ZJ. Synthesis 2005; 19
8c Proctor LD, Warr AJ. Org. Process Res. Dev. 2002; 6: 884

9 Jia M, Ma S. Angew. Chem. Int. Ed. 2016; 55: 9134
10 Burtoloso AC. B, Dias RM. P, Leonarczyk IA. Eur. J. Org. Chem. 2013; 5005
11 Trost BM, Melvin LS. Sulfur Ylides: Emerging Synthetic Intermediates . Academic Press; New York: 1975
12 Baldwin JE, Adlington RM, Godfrey CR. A, Gollins DW, Vaughan JG. J. Chem. Soc., Chem. Commun. 1993; 1434
13 Corey EJ, Chaykovsky M. J. Am. Chem. Soc. 1962; 84: 867
14 Corey EJ, Chaykovsky M. J. Am. Chem. Soc. 1964; 86: 1640

15a Johnson CR, Haake M, Schroeck CW. J. Am. Chem. Soc. 1970; 92: 6594
15b Johnson CR, Rogers PE. J. Org. Chem. 1973; 38: 1798
15c Johnson CR, Janiga ER, Haake M. J. Am. Chem. Soc. 1968; 90: 3890

16 Nozaki H, Tunemoto D, Matubara S, Kondô K. Tetrahedron 1967; 23: 545
17 Baldwin JE, Adlington RM, Godfrey CR. A, Gollins DW, Smith ML, Russel AT. Synlett 1993; 51
18 Kaiser C, Trost BM, Beeson J, Weinstock J. J. Org. Chem. 1965; 30: 3972
19 Ide J, Kishida Y. Tetrahedron Lett. 1966; 1787
20 Tamura Y, Miyamoto T, Nishimura T, Eiho J, Kita Y. J. Chem. Soc., Perkin Trans. 1 1974; 102
21 Bradbury RH, Gilchrist TL, Rees CW. J. Chem. Soc., Perkin Trans. 1 1981; 3225
22 Marino JP, Kaneko T. J. Org. Chem. 1974; 39: 3175
23 Tamuru Y, Miyamoto T, Kiyokawa H, Kita Y. J. Chem. Soc., Perkin Trans. 1 1974; 1125
24 Faragher R, Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 1977; 1196
25 Yamanaka H, Konno S, Sakamoto T, Niitsuma S, Noji S. Chem. Pharm. Bull. 1981; 29: 2837
26 Yamanaka H, Niitsuma S, Sakamoto T. Heterocycles 1978; 10
27 Ando W, Yagihara T, Tozune S, Nakaido S, Migita T. Tetrahedron Lett. 1969; 1979
28 Dost F, Gosselck J. Tetrahedron Lett. 1970; 5091
29 Moody CJ, Slawin AM. Z, Taylor RJ, Williams DJ. Tetrahedron Lett. 1988; 29: 6009
30 Zhu C, Yoshimura A, Ji L, Wei Y, Nemykin VN, Zhdankin VV. Org. Lett. 2012; 14: 3170
31 Vaitla J, Hopmann KH, Bayer A. Org. Lett. 2017; 19: 6688
32 Mangion IK, Nwamba IK, Shevlin M, Huffman MA. Org. Lett. 2009; 11: 3566
33 Vaitla J, Bayer A, Hopmann KH. Angew. Chem. Int. Ed. 2017; 56: 4277
34 Baratta W, Zotto AD. Chem. Commun. 1997; 2163
35 Yudin AK. Catalyzed Carbon–Heteroatom Bond Formation . Wiley-VCH; Weinheim, Germany: 2011
36 Doyle MP, McKervey MA, Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds . Wiley; New York: 1998
37 Trost BM. J. Am. Chem. Soc. 1967; 89: 138
38 Cohen T, Herman G, Chapman TM, Kuhn D. J. Am. Chem. Soc. 1974; 96: 5627
39 Cimetière B, Julia M. Synlett 1991; 271
40 Mangion IK, Weisel M. Tetrahedron Lett. 2010; 51: 5490
41 Mangion IK, Ruck RT, Rivera N, Huffman MA, Shevlin M. Org. Lett. 2011; 13: 5480
42 Molinaro C, Bulger PG, Lee EE, Kosjek B, Lau S, Gauvreau D, Howard ME, Wallace DJ, O’Shea PD. J. Org. Chem. 2012; 77: 2299
43 Phelps AM, Chan VS, Napolitano JG, Krabbe SW, Schomaker JM, Shekhar S. J. Org. Chem. 2016; 81: 4158
44 Cheng J, Wu X, Sun S, Yu J.-T. Synlett 2018;
45 Eberlin MN, Kascheres C. J. Org. Chem. 1988; 53: 2084
46 Barday M, Janot C, Halcovitch NR, Muir J, Aissa C. Angew. Chem. Int. Ed. 2017; 56: 13117
47 Xu Y, Zhou X, Zheng G, Li X. Org. Lett. 2017; 19: 5256
48 Xu Y, Yang X, Zhou X, Kong L, Li X. Org. Lett. 2017; 19: 4307
49 Zheng G, Tian M, Xu Y, Chen X, Li X. Org. Chem. Front. 2018; 5: 998
50 Cheng J, Yang R, Wu X, Sun S, Yu J.-T. Synthesis 2018; 50: 3487
51 Xie H, Lan J, Gui J, Chen F, Jiang H, Zeng W. Adv. Synth. Catal. 2018; 360: 3534
52 Chen G, Zhang X, Jia R, Li B, Fan X. Adv. Synth. Catal. 2018; 360: 3781
53 Halskov KS, Witten MR, Hoang GL, Mercado BQ, Ellman JA. Org. Lett. 2018; 20: 2464
54 Hoang GL, Ellman JA. Tetrahedron 2018; 74: 3318

55a Oh H, Han S, Pandey AK, Han SH, Mishra NK, Kim S, Chun R, Kim HS, Park J, Kim IS. J. Org. Chem. 2018; 83: 4070
55b Zhu J, Sun S, Cheng J. Tetrahedron Lett. 2018; 59: 2284

56 Wu X, Xiong H, Sun S, Cheng J. Org. Lett. 2018; 20: 1396
57 Hu P, Zhang Y, Xu Y, Yang S, Liu B, Li X. Org. Lett. 2018; 20: 2160
58 Xu Y, Zheng G, Yang X, Li X. Chem. Commun. 2018; 670
59 Suarez AI. O, del Río MP, Remerie K, Reek JN. H, de Bruin B. ACS Catal. 2012; 2: 2046