Recent Advances in the Generation of Onium Ylides for Sommelet–Hauser Rearrangements

Eiji Tayama

doi:10.1055/a-1914-7261

Synthesis, Table of Contents

Synthesis 2022; 54(24): 5385-5399
DOI: 10.1055/a-1914-7261

short review

Recent Advances in the Generation of Onium Ylides for Sommelet–Hauser Rearrangements

Authors

Eiji Tayama ∗

Abstract

All articles of this category

Abstract

The Sommelet–Hauser rearrangement of X-benzylic onium ylides (X = heteroatom) is an interesting transformation in organic synthesis. This rearrangement proceeds via dearomative [2,3]-sigmatropic rearrangement, followed by aromatization to form a carbon(sp²)–carbon(sp³) bond. Few advances were made in studies performed around 2000 on this rearrangement because of several competitive side reactions and structural limitations. However, studies performed in the last 15 years on the rearrangement have remarkably expanded the substrate scope and synthetic applications. In this review, the utility of the Sommelet–Hauser rearrangement and recent advances for the generation of onium ylides are described.

1 Introduction

2 Base-Induced Rearrangement

3 Transition-Metal-Catalyzed Rearrangement

4 Light-Mediated Rearrangement

5 Aryne-Induced Rearrangement

6 Conclusions and Outlook

Key words

rearrangements - Sommelet–Hauser - sigmatropic - dearomative [2,3] - onium ylides - onium salts

Full Text

References

References

For a review on the Sommelet–Hauser (S–H) rearrangement:

1a Nair VN, Tambar UK. Org. Biomol. Chem. 2022; 20: 3427
1b Tayama E. Chem. Rec. 2015; 15: 789

For representative reviews on onium ylide rearrangements taken up the S–H rearrangement:

2a Tayama E. Heterocycles 2016; 92: 793
2b Bach R, Harthong S, Lacour J. Nitrogen- and Sulfur-Based Stevens and Related Rearrangements . In Comprehensive Organic Synthesis II, Vol. 3, Chap. 3.20. Knochel P, Molander GA. Elsevier; Oxford: 2014: 992
2c Lahm G, Pacheco JC. O, Opatz T. Synthesis 2014; 46: 2413
2d Clayden J, Donnard M, Lefranc J, Tetlow DJ. Chem. Commun. 2011; 47: 4624
2e Sweeney JB. Chem. Soc. Rev. 2009; 38: 1027
2f Vanecko JA, Wan H, West FG. Tetrahedron 2006; 62: 1043
2g Kürti L, Czakó B. In Strategic Applications of Named Reactions in Organic Synthesis. Elsevier; Burlington MA: 2005: 422
2h Nitrogen, Oxygen and Sulfur Ylide Chemistry . Clark JS. Oxford University Press; Oxford: 2002
2i Markó IE. The Stevens and Related Rearrangements . In Comprehensive Organic Synthesis, Vol. 3, Chap. 3.10. Trost BM, Fleming I. Pergamon; Oxford: 1991: 913
2j Pine SH. Org. React. 1970; 18: 403

Theoretical studies:

3a Okada K, Tanaka M, Takagi R. J. Phys. Org. Chem. 2003; 16: 271
3b Heard GL, Yates BF. J. Org. Chem. 1996; 61: 7276

4 Sommelet M. C. R. Hebd. Sceances Acad. Sci. 1937; 205: 56

In a previous review (ref. 2i), Ingold and Jessop’s study on the sulfonium ylide in 1930 was presented as the first example of the S–H rearrangement. Hughes and Kuriyan later reported a similar result in 1935. However, no product assignments were made in these reports. The assignments were made by Hilbert and Pinck in 1938. See:

5a Hilbert GE, Pinck LA. J. Am. Chem. Soc. 1938; 60: 494
5b Hughes ED, Kuriyan KI. J. Chem. Soc. 1935; 1609
5c Ingold CK, Jessop JA. J. Chem. Soc. 1930; 713

6a Klein KP, Van Eenam DN, Hauser CR. J. Org. Chem. 1967; 32: 1155
6b Puterbaugh WH, Hauser CR. J. Am. Chem. Soc. 1964; 86: 1108
6c Puterbaugh WH, Hauser CR. J. Am. Chem. Soc. 1964; 86: 1105
6d Jones GC, Beard WQ, Hauser CR. J. Org. Chem. 1963; 28: 199
6e Jones GC, Hauser CR. J. Org. Chem. 1962; 27: 3572
6f Beard WQ. Jr, Hauser CR. J. Org. Chem. 1961; 26: 371
6g Beard WQ. Jr, Hauser CR. J. Org. Chem. 1960; 25: 334
6h Lednicer D, Hauser CR. J. Am. Chem. Soc. 1957; 79: 4449
6i Brasen WR, Hauser CR. Org. Synth. 1954; 34: 61
6j Kantor SW, Hauser CR. J. Am. Chem. Soc. 1951; 73: 4122

Representative studies:

7a McComas CC, Van Vranken DL. Tetrahedron Lett. 2003; 44: 8203
7b Berger R, Ziller JW, Van Vranken DL. J. Am. Chem. Soc. 1998; 120: 841
7c Hori M, Kataoka T, Shimizu H, Kataoka M, Tomoto A, Kishida M. Tetrahedron Lett. 1983; 24: 3733
7d Hauser CR, Van Eenam DN. J. Org. Chem. 1958; 23: 865
7e Van Eenam DN, Hauser CR. J. Am. Chem. Soc. 1957; 79: 5520
7f Hauser CR, Van Eenam DN. J. Am. Chem. Soc. 1957; 79: 5512

Examples of base-induced S–H rearrangement of ammonium salts apart from Hauser and co-workers before 2007:

8a Couty F, David O, Drouillat B. Tetrahedron Lett. 2007; 48: 9180
8b Hanessian S, Talbot C, Saravanan P. Synthesis 2006; 723
8c Maeda Y, Sato Y. Chem. Pharm. Bull. 1998; 46: 508
8d Klunder JM. J. Heterocycl. Chem. 1995; 32: 1687
8e Zdrojewski T, Jończyk A. Tetrahedron Lett. 1995; 36: 1355
8f Jończyk A, Lipiak D. J. Org. Chem. 1991; 56: 6933
8g Jończyk A, Lipiak D, Sienkiewicz K. Synlett 1991; 493
8h Weinreb SM, Basha FZ, Hibino S, Khatri NA, Kim D, Pye WE, Wu T.-T. J. Am. Chem. Soc. 1982; 104: 536
8i Sato Y, Yagi Y, Koto M. J. Org. Chem. 1980; 45: 613
8j Bumgardner CL, Hsu H.-B, Afghahi F, Roberts WL, Purrington ST. J. Org. Chem. 1979; 44: 2348
8k Sanders EB, Secor HV, Seeman JI. J. Org. Chem. 1978; 43: 324
8l Kim D, Weinreb SM. J. Org. Chem. 1978; 43: 125
8m Sanders EB, Secor HV, Seeman JI. J. Org. Chem. 1976; 41: 2658
8n Giumanini AG, Trombini C, Lercker G. J. Org. Chem. 1976; 41: 2187
8o Mander LN, Turner JV. J. Org. Chem. 1973; 38: 2915
8p Julia S, Huynh C, Michelot D. Tetrahedron Lett. 1972; 13: 3587
8q Pine SH, Munemo EM, Phillips TR, Bartolini G, Cotton WD, Andrews GC. J. Org. Chem. 1971; 36: 984
8r Archer DA. J. Chem. Soc. C 1971; 1329
8s Grethe G, Lee HL, Uskoković MR. Tetrahedron Lett. 1969; 10: 1937
8t Anderson AG. Jr, Wills MT. J. Org. Chem. 1968; 33: 3046
8u Paul R, Tchelitcheff S. Bull. Chim. Soc. Fr. 1968; 2134
8v Pine SH. Tetrahedron Lett. 1967; 8: 3393
8w Wittig G, Streib H. Justus Liebigs Ann. Chem. 1953; 584: 1
8x Wittig G, Tenhaeff H, Schoch W, Koenig G. Justus Liebigs Ann. Chem. 1951; 572: 1

Examples of base-induced S–H rearrangement of sulfonium salts:

9a Okada K, Tanaka M. J. Chem. Soc., Perkin Trans. 1 2002; 2704
9b Ishibashi H, Tabata T, Kobayashi T, Takamuro I, Ikeda M. Chem. Pharm. Bull. 1991; 39: 2878
9c Yamamoto M, Kakinuma M, Kohmoto S, Yamada K. Bull. Chem. Soc. Jpn. 1989; 62: 958
9d Lee T.-J, Holtz WJ. Tetrahedron Lett. 1983; 24: 2071
9e Campbell SJ, Darwish D. Can. J. Chem. 1976; 54: 193
9f Hayashi Y, Oda R. Tetrahedron Lett. 1968; 9: 5381
9g See also ref. 8p

Examples of base-induced S–H rearrangement of in situ generated azasulfonium salts:

10a Alper PB, Nguyen KT. J. Org. Chem. 2003; 68: 2051
10b Karp GM, Condon ME. J. Heterocycl. Chem. 1994; 31: 1513
10c Warpehoski MA, Bradford VS. Tetrahedron Lett. 1986; 27: 2735
10d Gassman PG, Schenk WN. J. Org. Chem. 1977; 42: 3240
10e Gassman PG, Gruetzmacher G, van Bergen TJ. J. Am. Chem. Soc. 1974; 96: 5512
10f Gassman PG, van Bergen TJ. J. Am. Chem. Soc. 1974; 96: 5508
10g Gassman PG, van Bergen TJ, Gilbert DP, Cue BW. Jr. J. Am. Chem. Soc. 1974; 96: 5495
10h Gassman PG, van Bergen TJ, Gruetzmacher G. J. Am. Chem. Soc. 1973; 95: 6508
10i Gassman PG, van Bergen TJ. J. Am. Chem. Soc. 1973; 95: 2718
10j Gassman PG, van Bergen TJ. J. Am. Chem. Soc. 1973; 95: 591
10k Gassman PG, van Bergen TJ. J. Am. Chem. Soc. 1973; 95: 590
10l Gassman PG, Gruetzmacher G. J. Am. Chem. Soc. 1973; 95: 588

11 Reich Collection, Bordwell pK _a Table (accessed Aug 18, 2022):. https://organicchemistrydata.org/hansreich/resources/pka/

12a Vedejs E, West FG. Chem. Rev. 1986; 86: 941
12b Vedejs E, Martinez GR. J. Am. Chem. Soc. 1979; 101: 6452

13a Nishimura T, Zhang C, Maeda Y, Shirai N, Ikeda S, Sato Y. Chem. Pharm. Bull. 1999; 47: 267
13b Narita K, Shirai N, Sato Y. J. Org. Chem. 1997; 62: 2544
13c Zhang C, Maeda Y, Shirai N, Sato Y. J. Chem. Soc., Perkin Trans. 1 1997; 25
13d Tanzawa T, Shirai N, Sato Y, Hatano K, Kurono Y. J. Chem. Soc., Perkin Trans. 1 1995; 2845
13e Kawanishi N, Shirai N, Sato Y, Hatano K, Kurono Y. J. Org. Chem. 1995; 60: 4272
13f Maeda Y, Shirai N, Sato Y. J. Chem. Soc., Perkin Trans. 1 1994; 393
13g Sakuragi A, Shirai N, Sato Y, Kurono Y, Hatano K. J. Org. Chem. 1994; 59: 148
13h Sato Y, Shirai N, Machida Y, Ito E, Yasui T, Kurono Y, Hatano K. J. Org. Chem. 1992; 57: 6711
13i Kitano T, Shirai N, Motoi M, Sato Y. J. Chem. Soc., Perkin Trans. 1 1992; 2851
13j Tanaka T, Shirai N, Sugimori J, Sato Y. J. Org. Chem. 1992; 57: 5034
13k Kitano T, Shirai N, Sato Y. Chem. Pharm. Bull. 1992; 40: 768
13l Tanaka T, Shirai N, Sato Y. Chem. Pharm. Bull. 1992; 40: 518
13m Kitano T, Shirai N, Sato Y. Synthesis 1991; 996
13n Sumiya F, Shirai N, Sato Y. Chem. Pharm. Bull. 1991; 39: 36
13o Shirai N, Watanabe Y, Sato Y. J. Org. Chem. 1990; 55: 2767
13p Shirai N, Sumiya F, Sato Y, Hori M. J. Org. Chem. 1989; 54: 836
13q Sugiyama H, Sato Y, Shirai N. Synthesis 1988; 988
13r Shirai N, Sumiya F, Sato Y, Hori M. J. Chem. Soc., Chem. Commun. 1988; 370
13s Shirai N, Sato Y. J. Org. Chem. 1988; 53: 194
13t Nakano M, Sato Y. J. Org. Chem. 1987; 52: 1844
13u Nakano M, Sato Y. J. Chem. Soc., Chem. Commun. 1985; 1684

14 Sato Y, Sakakibara H. J. Organomet. Chem. 1979; 166: 303
15 Maeda Y, Sato Y. J. Org. Chem. 1996; 61: 5188

16a Robert A, Lucas-Thomas M.-T. J. Chem. Soc., Chem. Commun. 1980; 629
16b Robert A, Thomas MT, Foucaud A. J. Chem. Soc., Chem. Commun. 1979; 1048

17 A previous study on the structure of carbonyl-stabilized ammonium ylides: Bailey NA, Hull SE, Kersting GF, Morrison J. Chem. Commun. 1971; 1429
18 Tayama E, Kimura H. Angew. Chem. Int. Ed. 2007; 46: 8869
19 Tayama E, Takedachi K, Iwamoto H, Hasegawa E. Tetrahedron 2010; 66: 9389

20a Tayama E, Sato R, Ito M, Iwamoto H, Hasegawa E. Heterocycles 2013; 87: 381
20b Tayama E, Sato R, Takedachi K, Iwamoto H, Hasegawa E. Tetrahedron 2012; 68: 4710
20c Tayama E, Otoyama S, Tanaka H. Tetrahedron: Asymmetry 2009; 20: 2600
20d Tayama E, Orihara K, Kimura H. Org. Biomol. Chem. 2008; 6: 3673

21 Biswas B, Singleton DA. J. Am. Chem. Soc. 2015; 137: 14244
22 Mita T, Sugawara M, Sato Y. J. Org. Chem. 2016; 81: 5236
23 Casoni G, Myers EL, Aggarwal VK. Synthesis 2016; 48: 3241
24 Colgan AC, Müller-Bunz H, McGarrigle EM. J. Org. Chem. 2016; 81: 11394
25 Tayama E, Watanabe K, Matano Y. Eur. J. Org. Chem. 2016; 3631
26 Tayama E, Watanabe K, Sotome S. Org. Biomol. Chem. 2017; 15: 6668
27 Tayama E, Sotome S. Org. Biomol. Chem. 2018; 16: 4833
28 Tayama E, Hirano K, Baba S. Tetrahedron 2020; 76: 131064
29 Zhang L, Cheng S, Hu H, Xu D. Asian J. Chem. 2019; 31: 3009
30 Previous reports, see refs. 8d, 8h, 8k, 8l, 8m, 8u, and 13f.
31 Tayama E, Shimizu G, Nakao R. Tetrahedron 2022; 111: 132721
32 A representative review: Jana S, Guo Y, Koenigs RM. Chem. Eur. J. 2021; 27: 1270
33 Aggarwal VK, Smith HW, Hynd G, Jones RV. H, Fieldhouse R, Spey SE. J. Chem. Soc., Perkin Trans. 1 2000; 3267
34 Liao M, Peng L, Wang J. Org. Lett. 2008; 10: 693
35 Li Y, Shi Y, Huang Z, Wu X, Xu P, Wang J, Zhang Y. Org. Lett. 2011; 13: 1210
36 Xu X, Li C, Xiong M, Tao Z, Pan Y. Chem. Commun. 2017; 53: 6219
37 Yang Z, Guo Y, Koenigs RM. Chem. Commun. 2019; 55: 8410
38 Pan C, Guo W, Gu Z. Chem. Sci. 2018; 9: 5850
39 Previous reports under the fluoride-induced conditions, see ref. 13b, 13e, 13f, 13h, 13k, 13m, 13n, 13o, 13p, and 13r.
40 Jana S, Koenigs RM. Org. Lett. 2019; 21: 3653
41 Lin X, Yang W, Yang W, Liu X, Feng X. Angew. Chem. Int. Ed. 2019; 58: 13492
42 Li S.-S, Wang J. J. Org. Chem. 2020; 85: 12343
43 Li F, He F, Koenigs RM. Synthesis 2019; 51: 4348
44 Yang Z, Guo Y, Koenigs RM. Chem. Eur. J. 2019; 25: 6703
45 A representative review: Roy T, Biju AT. Chem. Commun. 2018; 54: 2580

Representative initial studies:

46a Blackburn GM, Ollis WD, Smith C, Sutherland IO. Chem. Commun. 1969; 99
46b Ehrhart G, Seidl G. Chem. Ber. 1964; 97: 1994
46c Hellmann H, Eberle D. Justus Liebigs Ann. Chem. 1963; 662: 188
46d Hellmann H, Scheytt GM. Justus Liebigs Ann. Chem. 1961; 642: 22
46e Hellmann H, Unseld W. Justus Liebigs Ann. Chem. 1960; 631: 82
46f Wittig G, Benz E. Chem. Ber. 1959; 92: 1999

47 Roy T, Gaykar RN, Bhattacharjee S, Biju AT. Chem. Commun. 2019; 55: 3004
48 A representative example: Xu B, Tamber UK. Angew. Chem. Int. Ed. 2017; 56: 9868
49 A representative example: Blid J, Panknin O, Tuzina P, Somfai P. J. Org. Chem. 2007; 72: 1294
50 A representative example: West TH, Daniels DS. B, Slawin AM. Z, Smith AD. J. Am. Chem. Soc. 2014; 136: 4476
51 Garbi A, Allain L, Chorki F, Ourévitch M, Crousse B, Bonnet-Delpon D, Nakai T, Bégué J.-P. Org. Lett. 2001; 3: 2529