Enantioselective Intermolecular Murai-Type Alkene Hydroarylation Reactions

Timothy P. Aldhous; Raymond W. M. Chung; Andrew G. Dalling; John F. Bower

doi:10.1055/s-0040-1720406

Synthesis, Table of Contents

Synthesis 2021; 53(17): 2961-2975
DOI: 10.1055/s-0040-1720406

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Enantioselective Intermolecular Murai-Type Alkene Hydroarylation Reactions

Timothy P. Aldhous

^aSchool of Chemistry, University of Bristol, Bristol, BS8 1TS, UK

^bDepartment of Chemistry, University of Liverpool, Liverpool, L69 7ZD, UK

,

Raymond W. M. Chung

^bDepartment of Chemistry, University of Liverpool, Liverpool, L69 7ZD, UK

,

Andrew G. Dalling

^aSchool of Chemistry, University of Bristol, Bristol, BS8 1TS, UK

,

John F. Bower ∗

^bDepartment of Chemistry, University of Liverpool, Liverpool, L69 7ZD, UK

› Author Affiliations

Abstract

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Abstract

Strategies that enable the efficient assembly of complex building blocks from feedstock chemicals are of paramount importance to synthetic chemistry. Building upon the pioneering work of Murai and co-workers in 1993, C–H-activation-based enantioselective hydroarylations of alkenes offer a particularly promising framework for the step- and atom-economical installation of benzylic stereocenters. This short review presents recent intermolecular enantioselective Murai-type alkene hydroarylation methodologies and the mechanisms by which they proceed.

1 Introduction

2 Enantioselective Hydroarylation Reactions of Strained Bicyclic Alkenes

3 Enantioselective Hydroarylation Reactions of Electron-Rich Acyclic Alkenes

4 Enantioselective Hydroarylation Reactions of Electron-Poor Acyclic Alkenes

5 Enantioselective Hydroarylation Reactions of Minimally Polarized Acyclic Alkenes

6 Conclusion and Outlook

Key words

enantioselective - hydroarylation - C–H activation - catalysis - transition metal

Full Text

References

References
1 Harrington PJ, Lodewijk E. Org. Process Res. Dev. 1997; 1: 72
2 Zhang Q, Li J.-F, Tian G.-H, Zhang R.-X, Sun J, Suo J, Feng X, Fang D, Jiang X.-R, Shen J.-S. Tetrahedron: Asymmetry 2012; 23: 577
3 Lee SH, Kim IS, Li QR, Dong GR, Jeong LS, Jung YH. J. Org. Chem. 2011; 76: 10011
4 Taber GP, Pfisterer DM, Colberg JC. Org. Process Res. Dev. 2004; 8: 385
5 Imao D, Glasspoole BW, Laberge VS, Crudden CM. J. Am. Chem. Soc. 2009; 131: 5024
6 Li L, Zhao S, Joshi-Pangu A, Diane M, Biscoe MR. J. Am. Chem. Soc. 2014; 136: 14027
7 Swift EC, Jarvo ER. Tetrahedron 2013; 69: 5799
8 Leonori D, Aggarwal VK. Angew. Chem. Int. Ed. 2015; 54: 1082
9 Zhao S, Gensch T, Murray B, Niemeyer ZL, Sigman MS, Biscoe MR. Science 2018; 362: 670
10 Li L, Wang C.-Y, Huang R, Biscoe MR. Nat. Chem. 2013; 5: 607
11 Bonet A, Odachowski M, Leonori D, Essafi S, Aggarwal VK. Nat. Chem. 2014; 6: 584
12 Llaveria J, Leonori D, Aggarwal VK. J. Am. Chem. Soc. 2015; 137: 10958
13 Odachowski M, Bonet A, Essafi S, Conti-Ramsden P, Harvey JN, Leonori D, Aggarwal VK. J. Am. Chem. Soc. 2016; 138: 9521
14 Aichhorn S, Bigler R, Myers EL, Aggarwal VK. J. Am. Chem. Soc. 2017; 139: 9519
15 Ganesh V, Noble A, Aggarwal VK. Org. Lett. 2018; 20: 6144
16 Wilson CM, Ganesh V, Noble A, Aggarwal VK. Angew. Chem. Int. Ed. 2017; 56: 16318
17 Friis SD, Pirnot MT, Buchwald SL. J. Am. Chem. Soc. 2016; 138: 8372
18 Jia T, Cao P, Wang B, Lou Y, Yin X, Wang M, Liao J. J. Am. Chem. Soc. 2015; 137: 13760
19 Cheng X, Lu H, Lu Z. Nat. Commun. 2019; 10: 3549
20 Taylor BL. H, Harris MR, Jarvo ER. Angew. Chem. Int. Ed. 2012; 51: 7790
21 Zhou Q, Srinivas HD, Dasgupta S, Watson MP. J. Am. Chem. Soc. 2013; 135: 3307
22 Zhou Q, Cobb KM, Tan T, Watson MP. J. Am. Chem. Soc. 2016; 138: 12057
23 Li B, Li T, Aliyu MA, Li ZH, Tang W. Angew. Chem. Int. Ed. 2019; 58: 11355
24 Lundin PM, Fu GC. J. Am. Chem. Soc. 2010; 132: 11027
25 Lucas EL, Jarvo ER. Nat. Rev. Chem. 2017; 1: 0065
26 Kischel J, Jovel I, Mertins K, Zapf A, Beller M. Org. Lett. 2006; 8: 19
27 Sun H.-B, Li B, Hua R, Yin Y. Eur. J. Org. Chem. 2006; 4231
28 Lee SY, Villani-Gale A, Eichman CC. Org. Lett. 2016; 18: 5034
29 Poulsen TB, Jørgensen KA. Chem. Rev. 2008; 108: 2903
30 Rueping M, Nachtsheim BJ. Beilstein J. Org. Chem. 2010; 6: 6
31 Matsuzawa H, Miyake Y, Nishibayashi Y. Angew. Chem. Int. Ed. 2007; 46: 6488
32 Vicennati P, Cozzi PG. Eur. J. Org. Chem. 2007; 2248
33 Mühlthau F, Schuster O, Bach T. J. Am. Chem. Soc. 2005; 127: 9348
34 Mühlthau F, Stadler D, Goeppert A, Olah GA, Prakash GK. S, Bach T. J. Am. Chem. Soc. 2006; 128: 9668
35 Marcum JS, Roberts CC, Manan RS, Cervarich TN, Meek SJ. J. Am. Chem. Soc. 2017; 139: 15580
36 Wang H, Bai Z, Jiao T, Deng Z, Tong H, He G, Peng Q, Chen G. J. Am. Chem. Soc. 2018; 140: 3542
37 Podhajsky SM, Iwai Y, Cook-Sneathen A, Sigman MS. Tetrahedron 2011; 67: 4435
38 Chen Y.-G, Shuai B, Xu X.-T, Li Y.-Q, Yang Q.-L, Qiu H, Zhang K, Fang P, Mei T.-S. J. Am. Chem. Soc. 2019; 141: 3395
39 Mei T.-S, Patel HH, Sigman MS. Nature 2014; 508: 340
40 Zhang C, Santiago CB, Crawford JM, Sigman MS. J. Am. Chem. Soc. 2015; 137: 15668
41 Evano G, Theunissen C. Angew. Chem. Int. Ed. 2019; 58: 7202
42 Dong Z, Ren Z, Thompson SJ, Xu Y, Dong G. Chem. Rev. 2017; 117: 9333
43 Newton CG, Wang S.-G, Oliveira CC, Cramer N. Chem. Rev. 2017; 117: 8908
44 Chalk AJ, Harrod JF. J. Am. Chem. Soc. 1965; 87: 16
45 Matsubara T, Koga N, Musaev DG, Morokuma K. Organometallics 2000; 19: 2318
46 Sakaki S, Mizoe N, Sugimoto M. Organometallics 1998; 17: 2510
47 Sakaki S, Sumimoto M, Fukuhara M, Sugimoto M, Fujimoto H, Matsuzaki S. Organometallics 2002; 21: 3788
48 Zhang M, Hu L, Lang Y, Cao Y, Huang G. J. Org. Chem. 2018; 83: 2937
49 Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N, Murai S. Bull. Chem. Soc. Jpn. 1995; 68: 62
50 Kakiuchi F, Kochi T, Mizushima E, Murai S. J. Am. Chem. Soc. 2010; 132: 17741
51 Lewis LN, Smith JF. J. Am. Chem. Soc. 1986; 108: 2728
52 Murai S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N. Nature 1993; 336: 529
53 Nakao Y, Kashihara N, Kanyiva KS, Hiyama T. Angew. Chem. Int. Ed. 2010; 49: 4451
54 Uchimaru Y. Chem. Commun. 1999; 1133
55 Gao K, Yoshikai N. J. Am. Chem. Soc. 2011; 133: 400
56 Peneau A, Guillou C, Chabaud L. Eur. J. Org. Chem. 2018; 5777
57 Donets PA, Cramer N. Angew. Chem. Int. Ed. 2015; 54: 633
58 Tsai AS, Wilson RM, Harada H, Bergman RG, Ellman JA. Chem. Commun. 2009; 3910
59 Harada H, Thalji RK, Bergman RG, Ellman JA. J. Org. Chem. 2008; 73: 6772
60 Watzke A, Wilson RM, O’Malley SJ, Bergman RG, Ellman JA. Synlett 2007; 2383
61 Thalji RK, Ellman JA, Bergman RG. J. Am. Chem. Soc. 2004; 126: 7192
62 Diesel J, Finogenova AM, Cramer N. J. Am. Chem. Soc. 2018; 140: 4489
63 Sakamoto K, Nishimura T. Org. Biomol. Chem. 2021; 19: 684
64 Li G, Liu Q, Vasamsetty L, Guo W, Wang J. Angew. Chem. Int. Ed. 2020; 59: 3475
65 Li Z.-Y, Lakmal HH. C, Qian X, Zhu Z, Donnadieu B, McClain SJ, Xu X, Cui X. J. Am. Chem. Soc. 2019; 141: 15730
66 Wang Y.-X, Qi S.-L, Luan Y.-X, Han X.-W, Wang S, Chen H, Ye M. J. Am. Chem. Soc. 2018; 140: 5360
67 Shibata T, Ryu N, Takano H. Adv. Synth. Catal. 2015; 357: 1131
68 Shinde VS, Mane MV, Cavallo L, Rueping M. Chem. Eur. J. 2020; 26: 8308
69 Lu H.-H, Liu H, Wu W, Wang X.-F, Lu L.-Q, Xiao W.-J. Chem. Eur. J. 2009; 15: 2742
70 Huang H, Peters R. Angew. Chem. Int. Ed. 2009; 48: 604
71 Han X, Widenhoefer RA. Org. Lett. 2006; 8: 3801
72 Liu C, Zhu X, Zhang P, Yang H, Zhu C, Fu H. iScience 2018; 10: 11
73 Zhang Z.-M, Xu B, Qian Y, Wu L, Wu Y, Zhou L, Liu Y, Zhang J. Angew. Chem. Int. Ed. 2018; 57: 10373
74 Jang YJ, Larin EM, Lautens M. Angew. Chem. Int. Ed. 2017; 56: 11927
75 Zhang P, Tsuji N, Ouyang J, List B. J. Am. Chem. Soc. 2021; 143: 675
76 Aufdenblatten R, Diezi S, Togni A. Monatsh. Chem. 2000; 131: 1345
77 Tsuchikama K, Kasagawa M, Hashimoto Y.-K, Endo K, Shibata T. J. Organomet. Chem. 2008; 693: 3939
78 Shirai T, Yamamoto Y. Angew. Chem. Int. Ed. 2015; 54: 9894
79 Nagamoto M, Fukuda J.-I, Hatano M, Yorimitsu H, Nishimura T. Org. Lett. 2017; 19: 5952
80 Sevov CS, Hartwig JF. J. Am. Chem. Soc. 2013; 135: 2116
81 Ebe Y, Nishimura T. J. Am. Chem. Soc. 2015; 137: 5899
82 Ebe Y, Onoda M, Nishimura T, Yorimitsu H. Angew. Chem. Int. Ed. 2017; 56: 5607
83 Sakamoto K, Nishimura T. Adv. Synth. Catal. 2019; 361: 2124
84 Hatano M, Ebe Y, Nishimura T, Yorimitsu H. J. Am. Chem. Soc. 2016; 138: 4010
85 Yamauchi D, Nishimura T, Yorimitsu H. Chem. Commun. 2017; 53: 2760
86 Romero-Arenas A, Hornillos V, Iglesias-Sigüenza J, Fernández R, López-Serrano J, Ros A, Lassaletta JM. J. Am. Chem. Soc. 2020; 142: 2628
87 Shibata T, Michino M, Kurita H, Tahara Y.-K, Kanyiva KS. Chem. Eur. J. 2017; 23: 88
88 Shibata T, Kurita H, Onoda S, Kanyiva KS. Asian J. Org. Chem. 2018; 7: 1411
89 Satake S, Kurihara T, Nishikawa K, Mochizuki T, Hatano M, Ishihara K, Yoshino T, Matsunaga S. Nat. Catal. 2018; 1: 585
90 Potter TJ, Kamber DN, Mercado BQ, Ellman JA. ACS Catal. 2017; 7: 150
91 Potter TJ, Ellman JA. Org. Lett. 2017; 19: 2985
92 Filloux CM, Rovis T. J. Am. Chem. Soc. 2015; 137: 508
93 Shibata T, Shizuno T. Angew. Chem. Int. Ed. 2014; 53: 5410
94 Pan S, Ryu N, Shibata T. J. Am. Chem. Soc. 2012; 134: 17474
95 Lee P.-S, Yoshikai N. Org. Lett. 2015; 17: 22
96 Loup J, Zell D, Oliveira JC. A, Keil H, Stalke D, Ackermann L. Angew. Chem. Int. Ed. 2017; 56: 14197
97 Pesciaioli F, Dhawa U, Oliveira JC. A, Yin R, John M, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 15425
98 Grélaud S, Cooper P, Feron LJ, Bower JF. J. Am. Chem. Soc. 2018; 140: 9351