Recent Advances in the Smiles Rearrangement: New Opportunities for Arylation

David M. Whalley; Michael F. Greaney

doi:10.1055/a-1710-6289

Synthesis, Table of Contents

Synthesis 2022; 54(08): 1908-1918
DOI: 10.1055/a-1710-6289

short review

Recent Advances in the Smiles Rearrangement: New Opportunities for Arylation

Authors

David M. Whalley
Michael F. Greaney∗

Abstract

All articles of this category

Abstract

The Smiles rearrangement has undergone a renaissance in recent years providing new avenues for non-canonical arylation techniques in both the radical and polar regimes. This short review will discuss recent applications of the reaction (from 2017 to late 2021), including its relevance to areas such as heterocycle synthesis and the functionalization of alkenes and alkynes as well as glimpses at new directions for the field.

1 Introduction

2 Polar Smiles Rearrangements

3 Radical Smiles: Alkene and Alkyne Functionalization

4 Radical Smiles: Rearrangements via C–X Bond Cleavage

5 Radical Smiles: Miscellaneous Rearrangements

6 Conclusions

Key words

rearrangements - arylation - radicals - Smiles

Full Text

References

References
1 Snape TJ. Chem. Soc. Rev. 2008; 37: 2452
2 Holden CM, Greaney MF. Chem. Eur. J. 2017; 23: 8992
3 Henderson AR. P, Kosowan JR, Wood TE. Can. J. Chem. 2017; 95: 483
4 Allart-Simon I, Gérard S, Sapi J. Molecules 2016; 21: 878
5 Allen AR, Noten EA, Stephenson CR. J. Chem. Rev. 2021; 122, 2: 2695
6 Huynh M, De Abreu M, Belmont P, Brachet E. Chem. Eur. J. 2021; 27: 3581
7 Warren AL, Smiles S. J. Chem. Soc. 1931; 914
8 Levy AA, Rains HC, Smiles S. J. Chem. Soc. 1931; 3264
9 Naito T, Dohmori R, Nagase O. J. Pharm. Soc. Jpn. 1954; 74: 593
10 Naito T, Dohmori R, Shimoda M. Pharm. Bull. 1955; 3: 34
11 Truce WE, Ray WJ, Norman OL, Eickemeyer DB. J. Am. Chem. Soc. 1958; 80: 3625
12 Loven R, Speckamp WN. Tetrahedron Lett. 1972; 13: 1567
13 Köhler JJ, Speckamp WN. Tetrahedron Lett. 1977; 18: 631
14 Motherwell WB, Pennell AM. K. J. Chem. Soc., Chem. Commun. 1991; 877
15 Da Mata ML. E. N, Motherwell WB, Ujjainwalla F. Tetrahedron Lett. 1997; 38: 137
16 Da Mata ML. E. N, Motherwell WB, Ujjainwalla F. Tetrahedron Lett. 1997; 38: 141
17 Bonfand E, Forslund L, Motherwell WB, Vázquez S. Synlett 2000; 475
18 Waldau E, Pütter R. Angew. Chem. Int. Ed. 1972; 11: 826
19 Rasheed OK, Hardcastle IR, Raftery J, Quayle P. Org. Biomol. Chem. 2015; 13: 8048
20 Holden CM, Sohel SM. A, Greaney MF. Angew. Chem. Int. Ed. 2016; 55: 2450
21 Dey C, Katayev D, Ylijoki KE. O, Kündig EP. Chem. Commun. 2012; 48: 10957
22 Brachet E, Marzo L, Selkti M, König B, Belmont P. Chem. Sci. 2016; 7: 5002
23 Pudlo M, Allart-Simon I, Tinant B, Gérard S, Sapi J. Chem. Commun. 2012; 48: 2442
24 Clayden J, Farnaby W, Grainger DM, Hennecke U, Mancinelli M, Tetlow DJ, Hillier IH, Vincent MA. J. Am. Chem. Soc. 2009; 131: 3410
25 Clayden J, Donnard M, Lefranc J, Minassi A, Tetlow DJ. J. Am. Chem. Soc. 2010; 132: 6624
26 Atkinson RC, Fernández-Nieto F, Mas Rosellõ J, Clayden J. Angew. Chem. Int. Ed. 2015; 54: 8961
27 Abrams R, Jesani MH, Browning A, Clayden J. Angew. Chem. Int. Ed. 2021; 60: 11272
28 Costil R, Lefebvre Q, Clayden J. Angew. Chem. Int. Ed. 2017; 56: 14602
29 Millward MJ, Ellis E, Ward JW, Clayden J. Chem. Sci. 2021; 12: 2091
30 Cativiela C, Díaz-de-Villegas MD. Tetrahedron: Asymmetry 2007; 18: 569
31 Leonard DJ, Ward JW, Clayden J. Nature 2018; 562: 105
32 Barlow HL, Rabet PT. G, Durie A, Evans T, Greaney MF. Org. Lett. 2019; 21: 9033
33 Chu X.-Q, Ge D, Cui Y.-Y, Shen Z.-L, Li C.-J. Chem. Rev. 2021; 121: 12548
34 Kang L, Wang F, Zhang J, Yang H, Xia C, Qian J, Jiang G. Org. Lett. 2021; 23: 1669
35 Matsuzawa T, Hosoya T, Yoshida S. Org. Lett. 2021; 23: 2347
36 Pluta K, Jeleń M, Morak-Młodawska B. J. Mol. Struct. 2020; 1204
37 Flanigan DM, Romanov-Michailidis F, White NA, Rovis T. Chem. Rev. 2015; 115: 9307
38 Janssen-Müller D, Singha S, Lied F, Gottschalk K, Glorius F. Angew. Chem. Int. Ed. 2017; 56: 6276
39 Yasui K, Kamitani M, Fujimoto H, Tobisu M. Org. Lett. 2021; 23: 1572
40 An JM, Kang S, Huh E, Kim Y, Lee D, Jo H, Joung JF, Kim VJ, Lee JY, Dho YS, Jung Y, Hur JK, Park C, Jung J, Huh Y, Ku JL, Kim S, Chowdhury T, Park S, Kang JS, Oh MS, Park CK, Kim D. Chem. Sci. 2020; 11: 5658
41 Weller M, Wick W, Aldape K, Brada M, Berger M, Pfister SM, Nishikawa R, Rosenthal M, Wen PY, Stupp R, Reifenberger G. Nat. Rev. Dis. Prim. 2015; 1: 15017
42 Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
43 Tu J.-L, Tang W, Liu F. Org. Chem. Front. 2021; 8: 3712
44 Hu XQ, Chen JR, Wei Q, Liu FL, Deng QH, Beauchemin AM, Xiao WJ. Angew. Chem. Int. Ed. 2014; 53: 12163
45 Monos TM, McAtee RC, Stephenson CR. J. Science 2018; 361: 1369
46 Whalley DM, Duong HA, Greaney MF. Chem. Eur. J. 2019; 25: 1927
47 Abrams R, Clayden J. Angew. Chem. Int. Ed. 2020; 59: 11600
48 Kong W, Casimiro M, Merino E, Nevado C. J. Am. Chem. Soc. 2013; 135: 14480
49 Kong W, Casimiro M, Fuentes N, Merino E, Nevado C. Angew. Chem. Int. Ed. 2013; 52: 13086
50 Kong W, Merino E, Nevado C. Angew. Chem. Int. Ed. 2014; 53: 5078
51 Kong W, Fuentes N, García-Domínguez A, Merino E, Nevado C. Angew. Chem. Int. Ed. 2015; 54: 2487
52 Fuentes N, Kong W, Fernández-Sánchez L, Merino E, Nevado C. J. Am. Chem. Soc. 2015; 137: 964
53 Hervieu C, Kirillova MS, Suárez T, Müller M, Merino E, Nevado C. Nat. Chem. 2021; 13: 327
54 Chen F, Shao Y, Li M, Yang C, Su SJ, Jiang H, Ke Z, Zeng W. Nat. Commun. 2021; 12: 3304
55 Wang ZS, Chen YB, Zhang HW, Sun Z, Zhu C, Ye LW. J. Am. Chem. Soc. 2020; 142: 3636
56 Gao X, Li C, Yuan Y, Xie X, Zhang Z. Org. Biomol. Chem. 2020; 18: 263
57 Yan J, Cheo HW, Teo WK, Shi X, Wu H, Idres SB, Deng LW, Wu J. J. Am. Chem. Soc. 2020; 142: 11357
58 Fuss D, Wu YQ, Grossi MR, Hollett JW, Wood TE. J. Phys. Org. Chem. 2018; 31: e3742
59 De Abreu M, Belmont P, Brachet E. J. Org. Chem. 2021; 86: 3758
60 Alpers D, Cole KP, Stephenson CR. J. Angew. Chem. Int. Ed. 2018; 57: 12167
61 Gillaizeau-Simonian N, Barde E, Guérinot A, Cossy J. Chem. Eur. J. 2021; 27: 4004
62 Friese FW, Mück-Lichtenfeld C, Studer A. Nat. Commun. 2018; 9: 2808
63 Radhoff N, Studer A. Angew. Chem. Int. Ed. 2021; 60: 3561
64 Liang S, Wei K, Lin Y, Liu T, Wei D, Han B, Yu W. Org. Lett. 2021; 23: 4527
65 Faderl C, Budde S, Kachkovskyi G, Rackl D, Reiser O. J. Org. Chem. 2018; 83: 12192
66 Johnson S, Kovács E, Greaney MF. Chem. Commun. 2020; 56: 3222
67 Ruzi R, Ma J, Yuan XA, Wang W, Wang S, Zhang M, Dai J, Xie J, Zhu C. Chem. Eur. J. 2019; 25: 12724
68 Motherwell WB, Vazquez S. Tetrahedron Lett. 2000; 41: 9667
69 Li J, Liu Z, Wu S, Chen Y. Org. Lett. 2019; 21: 2077
70 Gonzalez-Gomez JC, Ramirez NP, Lana-Villarreal T, Bonete P. Org. Biomol. Chem. 2017; 15: 9680
71 Xia ZH, Dai L, Gao ZH, Ye S. Chem. Commun. 2020; 56: 1525
72 Dou Q, Li CJ, Zeng H. Chem. Sci. 2020; 11: 5740
73 Lardy SW, Luong KC, Schmidt VA. Chem. Eur. J. 2019; 25: 15267
74 Lawson CA, Dominey AP, Williams GD, Murphy JA. Chem. Commun. 2020; 56: 11445
75 Chang X, Zhang Q, Guo C. Org. Lett. 2019; 21: 4915
76 Liu C, Jiang Q, Lin Y, Fang Z, Guo K. Org. Lett. 2020; 22: 795
77 Whalley DM, Seayad J, Greaney MF. Angew. Chem. Int. Ed. 2021; 60: 22219