C–C Bond Activations of Minimally Activated Cyclopropanes

Olga O. Sokolova; Andrew G. Dalling; John F. Bower

doi:10.1055/s-0042-1753177

Synlett, Table of Contents

Synlett 2023; 34(12): 1317-1326
DOI: 10.1055/s-0042-1753177

account

Special Issue Honoring Masahiro Murakami’s Contributions to Science

C–C Bond Activations of Minimally Activated Cyclopropanes

Olga O. Sokolova

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

,

Andrew G. Dalling

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

,

John F. Bower∗

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

› Author Affiliations

Abstract

All articles of this category

Abstract

Catalytic processes involving oxidative addition of a C–C bond to a transition metal allow the atom economical assembly of complex scaffolds. The focus of this Account is on C–C bond activation-based methodologies that employ minimally activated cyclopropanes.

Keywords

C–C bond activation - oxidative addition - cyclopropanes

Full Text

References

References
1 C-C Bond Activation. In Topics in Current Chemistry. Dong G. Springer; Berlin: 2014
2 Souillart L, Cramer N. Chem. Rev. 2015; 115: 9410
3 Fumagalli G, Stanton S, Bower JF. Chem. Rev. 2017; 117: 9404
4 Murakami M, Ishida N. J. Am. Chem. Soc. 2016; 138: 13759
5 Kim D.-S, Park W.-J, Jun C.-H. Chem. Rev. 2017; 117: 8977
6 Chen P.-H, Billett BA, Tsukamoto T, Dong G. ACS Catal. 2017; 7: 1340
7 Song F, Gou T, Wang B.-Q, Shi Z.-J. Chem. Soc. Rev. 2018; 47: 7078
8 To CT, Chan KS. Eur. J. Org. Chem. 2019; 6581
9 Deng L, Dong G. Trends Chem. 2020; 2: 183
10 Tipper CF. H. J. Chem. Soc. 1955; 2045
11 Crabtree RH. Chem. Rev. 1985; 85: 245
12 Rybtchinski B, Milstein D. Angew. Chem. Int. Ed. 1999; 38: 870
13 Low JJ, Goddard WA. J. Am. Chem. Soc. 1984; 106: 8321
14 Siegbahn PE. M, Blomberg MR. A. J. Am. Chem. Soc. 1992; 114: 10548
15 Halpern J. Acc. Chem. Res. 1982; 15: 238
16 O’Reilly ME, Dutta S, Veige AS. Chem. Rev. 2016; 116: 8105
17 Walsh AD. Nature 1947; 159: 165
18 Wu W, Ma B, Wu JI.-C, Schleyer P. vR, Mo Y. Chem. Eur. J. 2009; 15: 9730
19 Alabugin IV, Manoharan M. J. Comput. Chem. 2007; 28: 373
20 Brandi A, Cicchi S, Cordero FM, Goti A. Chem. Rev. 2014; 114: 7317
21 Yu L.-Z, Chen K, Zhu Z.-Z, Shi M. Chem. Commun. 2017; 53: 5935
22 Inglesby PA, Evans PA. Chem. Soc. Rev. 2010; 39: 2791
23 Ganesh V, Chandrasekaran S. Synthesis 2016; 48: 4347
24 Wender PA, Takahashi H, Witulski B. J. Am. Chem. Soc. 1995; 117: 4720
25 Noyori R, Odagi T, Takaya H. J. Am. Chem. Soc. 1970; 92: 5780
26 Noyori R, Kumagai Y, Umeda I, Takaya H. J. Am. Chem. Soc. 1972; 94: 4018
27 Delgado A, Rodríguez JR, Castedo L, Mascareñas JL. J. Am. Chem. Soc. 2003; 125: 9282
28 Evans PA, Inglesby PA. J. Am. Chem. Soc. 2008; 130: 12838
29 Li C, Zhang H, Feng J, Zhang Y, Wang J. Org. Lett. 2010; 12: 3082
30 Matsuda T, Tsuboi T, Murakami M. J. Am. Chem. Soc. 2007; 129: 12596
31 Roundhill DM, Lawson DN, Wilkinson G. J. Chem. Soc. A 1968; 845
32 Powell KG, McQuillin FJ. J. Chem. Soc. D 1971; 931
33 McQuillin FJ, Powell KC. J. Chem. Soc., Dalton Trans. 1972; 2129
34 Bart SC, Chirik PJ. J. Am. Chem. Soc. 2003; 125: 886
35 Koga Y, Narasaka K. Chem. Lett. 1999; 28: 705
36 Blanco-Urgoiti J, Añorbe L, Pérez-Serrano L, Domínguez G, Pérez-Castells J. Chem. Soc. Rev. 2004; 33: 32
37 Iqbal AF. M. Tetrahedron Lett. 1971; 3381
38 Shaw MH, Melikhova EY, Kloer DP, Whittingham WG, Bower JF. J. Am. Chem. Soc. 2013; 135: 4992
39 Shaw MH, McCreanor NG, Whittingham WG, Bower JF. J. Am. Chem. Soc. 2015; 137: 463
40 Shaw MH, Whittingham WG, Bower JF. Tetrahedron 2016; 72: 2731
41 Huang C.-Y, Doyle AG. J. Am. Chem. Soc. 2012; 134: 9541
42 Sokolova OO, Bower JF. Angew. Chem. Int. Ed. 2022; e202205007
43 Bi X, Zhang Q, Gu Z. Chin. J. Chem. 2021; 39: 1397
44 Shaw MH, Croft RA, Whittingham WG, Bower JF. J. Am. Chem. Soc. 2015; 137: 8054
45 Zhang Y.-L, Guo R.-T, He J.-H, Wang X.-C. Org. Lett. 2019; 21: 4239
46 McCreanor NG, Stanton S, Bower JF. J. Am. Chem. Soc. 2016; 138: 11465
47 Wang G.-W, Bower JF. J. Am. Chem. Soc. 2018; 140: 2743
48 Boyd O, Wang G.-W, Sokolova OO, Calow AD. J, Bertrand SM, Bower JF. Angew. Chem. Int. Ed. 2019; 58: 18844
49 Wang G.-W, Boyd O, Young TA, Bertrand SM, Bower JF. J. Am. Chem. Soc. 2020; 142: 1740
50 Wang G.-W, Sokolova OO, Young TA, Christodoulou EM. S, Butts CP, Bower JF. J. Am. Chem. Soc. 2020; 142: 19006
51 Dalling AG, Yamauchi T, McCreanor NG, Cox L, Bower JF. Angew. Chem. Int. Ed. 2019; 58: 221
52 Zhang Y, Chen Z, Xiao Y, Zhang J. Chem. Eur. J. 2009; 15: 5208
53 Liu L, Montgomery J. J. Am. Chem. Soc. 2006; 128: 5348
54 Ogoshi S, Nagata M, Kurosawa H. J. Am. Chem. Soc. 2006; 128: 5350
55 Liu L, Montgomery J. Org. Lett. 2007; 9: 3885
56 Tamaki T, Nagata M, Ohashi M, Ogoshi S. Chem. Eur. J. 2009; 15: 10083
57 Tamaki T, Ohashi M, Ogoshi S. Angew. Chem. Int. Ed. 2011; 50: 12067
58 Liu Q.-S, Wang D.-Y, Yang Z.-J, Luan Y.-X, Yang J.-F, Li J.-F, Pu Y.-G, Ye M. J. Am. Chem. Soc. 2017; 139: 18150
59 Wang G.-W, McCreanor NG, Shaw MH, Whittingham WG, Bower JF. J. Am. Chem. Soc. 2016; 138: 13501
60 Calow AD. J, Dailler D, Bower JF. J. Am. Chem. Soc. 2022; 144: 11069
61 Asako S, Kobashi T, Takai K. J. Am. Chem. Soc. 2018; 140: 15425
62 Kondo H, Miyamura S, Matsushita K, Kato H, Kobayashi C, Arifin, Itami K, Yokogawa D, Yamaguchi J. J. Am. Chem. Soc. 2020; 142: 11306
63 Kondo H, Itami K, Yamaguchi J. Chem. Sci. 2017; 8: 3799
64 Wang T, Wang M, Wang Y, Li M, Zheng Y, Chen Q, Zhao Y, Shi Z. Chem 2022; in press