Ground State Cross-Coupling of Haloarenes with Arenes Initiated by Organic Electron Donors, Formed in situ: An Overview

Giuseppe Nocera; John A. Murphy

doi:10.1055/s-0039-1690614

Synthesis, Table of Contents

Synthesis 2020; 52(03): 327-336
DOI: 10.1055/s-0039-1690614

short review

Ground State Cross-Coupling of Haloarenes with Arenes Initiated by Organic Electron Donors, Formed in situ: An Overview

Giuseppe Nocera

,

John A. Murphy∗

Abstract

All articles of this category

Abstract

Many reactions have been discovered that lead to coupling of haloarenes to arenes using potassium tert-butoxide as the base, and one of a variety of organic compounds as an additive. The organic additive reacts with the base to form a strong organic electron donor in situ that initiates a base-induced homolytic aromatic substitution (BHAS) coupling reaction, by converting the haloarene into an aryl radical. This brief report presents an overview of the wide range of organic additives that can be used, and the organic electron donors that they form.

Key words

electron transfer - initiation - BHAS coupling - organic electron donor - radical reaction

Full Text

References

References
1 Yanagisawa S, Ueda K, Taniguchi T, Itami K. Org. Lett. 2008; 10: 4673
2 Liu W, Cao H, Zhang H, Chung KH, He C, Wang H, Kwong FY, Lei A. J. Am. Chem. Soc. 2010; 132: 16737
3 Bunnett JF, Creary X. J. Org. Chem. 1974; 39: 3611
4 Sun CL, Li H, Yu D.-G, Yu M, Zhou X, Lu X.-Y, Huang K, Zheng S.-F, Li Z.-B, Shi J. Nat. Chem. 2010; 2: 1044
5 Roman DS, Takahashi Y, Charette AB. Org. Lett. 2011; 13: 3242
6 Shirakawa E, Itoh K.-I, Higashino T, Hayashi T. J. Am. Chem. Soc. 2010; 132: 15537
7 Studer A, Curran DP. Angew. Chem. Int. Ed. 2011; 50: 5018
8 Sun CL, Gu Y.-F, Wang B, Shi Z.-J. Chem. Eur. J. 2011; 17: 10844
9 De S, Ghosh S, Bhunia S, Sheikh JA, Bisai A. Org. Lett. 2012; 14: 4466
10 Wu Y, Wong SM, Mao F, Chan TL, Kwong FY. Org. Lett. 2012; 14: 5306
11 Chen W.-C, Hsu Y.-C, Shih W.-C, Lee C.-Y, Chuang W.-H, Tsai Y.-F, Chen PP.-Y, Ong T.-G. Chem. Commun. 2012; 48: 6702
12 A likely mode of action of arylhydrazines has been proposed, see: Dewanji A, Murarka S, Curran DP, Studer A. Org. Lett. 2013; 15: 6102
13 Liu W, Tian F, Wang X, Yu H, Bi Y. Chem. Commun. 2013; 49: 2983
14 Tanimoro K, Ueno M, Takeda K, Kirihata M, Tanimori S. J. Org. Chem. 2012; 77: 7844
15 Zhou S, Doni E, Anderson GM, Kane RG, MacDougall SW, Ironmonger VM, Tuttle T, Murphy JA. J. Am. Chem. Soc. 2014; 136: 17818
16 Ng YS, Chan CS, Chan KS. Tetrahedron Lett. 2012; 53: 3911
17 Zhao H, Shen J, Guo J, Ye R, Zeng H. Chem. Commun. 2013; 49: 2323
18 Zhao H, Shen J, Ren C, Zeng W, Zeng H. Org. Lett. 2017; 19: 2190
19 Paira R, Singh B, Hota PK, Ahmed J, Sau SC, Johnpeter JP, Mandal SK. J. Org. Chem. 2016; 81: 2432
20 Banik A, Paira R, Shaw BK, Vijaykumar G, Mandal SK. J. Org. Chem. 2018; 83: 3236
21 Yong G.-P, She W.-L, Zhang Y.-M, Li Y.-Z. Chem. Commun. 2011; 47: 11766
22 Qiu Y, Liu Y, Yang K, Hong W, Li Z, Wang Z, Yao Z, Jiang S. Org. Lett. 2011; 13: 3556
23 Wu Y, Choy PY, Kwong FY. Org. Biomol. Chem. 2014; 12: 6820
24 Barham JP, Coulthard G, Kane RG, Delgado N, John MP, Murphy JA. Angew. Chem. Int. Ed. 2016; 55: 4492
25 Zhang L, Yang H, Jiao L. J. Am. Chem. Soc. 2016; 138: 7151
26 Murphy JA, Khan TA, Zhou S.-Z, Thomson DW, Mohan M. Angew. Chem. Int. Ed. 2005; 44: 1356
27 Murphy JA, Zhou S.-Z, Thomson DW, Schoenebeck F, Mohan M, Park SR, Tuttle T, Berlouis LE. A. Angew. Chem. Int. Ed. 2007; 46: 5178
28 Zhou S, Anderson GM, Mondal B, Doni E, Ironmonger V, Kranz M, Tuttle T, Murphy JA. Chem. Sci. 2014; 5: 476 ; the benzyne initiation proposed here may be responsible for other couplings seen in the absence of organic additives, see ref. 9
29 Gassman PG, Benecke HP. Tetrahedron Lett. 1969; 10: 1089
30 Bowne AT, Christopher TA, Levin RH. Tetrahedron Lett. 1976; 14: 4111
31 Yamabe S, Minato T, Ishiwata A, Irinamihira O, Machiguchi T. J. Org. Chem. 2007; 72: 2832
32 Okuma K, Sonoda S, Koga Y, Shioji K. J. Chem. Soc., Perkin Trans. 1 1999; 2997
33 Leadbeater NE. Nat. Chem. 2010; 2: 1007
34 Cuthbertson J, Gray VJ, Wilden JD. Chem. Commun. 2014; 50: 2575
35 Yi H, Jutand A, Lei A. Chem Commun. 2015; 51: 545
36 Shan X.-H, Yang B, Zheng H.-X, Qu J.-P, Kang Y.-B. Org. Lett. 2018; 20: 7898
37 Poonpatana P, dos Passos Gomes G, Hurrle T, Chardon K, Bräse S, Masters K.-S, Alabugin I. Chem. Eur. J. 2017; 23: 9091
38 Barham JP, Dalton SE, Allison M, Nocera G, Young A, John MP, McGuire T, Campos S, Tuttle T, Murphy JA. J. Am. Chem. Soc. 2018; 140: 11510
39 Yang H, Chu D.-Z, Jiao L. Chem. Sci. 2018; 9: 1534
40 Yang H, Zhang L, Jiao L. Chem. Eur. J. 2017; 23: 65
41 Scamehorn RG, Bunnett JF. J. Org. Chem. 1977; 42: 1449
42 Scamehorn RG, Hardacre JM, Lukanich JM, Sharpe LR. J. Org. Chem. 1984; 49: 4881
43 Guastavino JV, Rossi RA. J. Org. Chem. 2012; 77: 460
44 Zhao H, Xu X, Wu W, Zhang Y. Catal. Commun. 2018; 111: 95
45 Patil M. J. Org. Chem. 2016; 81: 632
46 Budén ME, Guastavino JF, Rossi RA. Org. Lett. 2013; 15: 1174
47 Budén ME, Bardagí JI, Puiatti M, Rossi RA. J. Org. Chem. 2017; 82: 8325
48 Rajan S, Muralimohan K. Tetrahedron Lett. 1978; 19: 483
49 Øpstad CL, Melø T.-B, Sliwka H.-R, Partali V. Tetrahedron 2009; 65: 7616
50 Zhang M.-X, Hu X.-H, Xu Y.-H, Loh T.-P. Asian J. Org. Chem. 2015; 4: 1047
51 Xu Z, Gao L, Wang L, Gong M, Wang W, Yuan R. ACS Catal. 2015; 5: 45
52 Nocera G, Young A, Palumbo F, Emery KJ, Coulthard G, McGuire T, Tuttle T, Murphy JA. J. Am. Chem. Soc. 2018; 140: 9751
53 Barham JP, Coulthard G, Emery KJ, Doni E, Cumine F, Nocera G, John MP, Berlouis LE. A, McGuire TM, Tuttle T, Murphy JA. J. Am. Chem. Soc. 2016; 138: 7402