Biaryl Synthesis via Electrooxidative Transition-Metal-Catalyzed C–H Activation

Jonas F. Goebel; Zhongyi Zeng; Lukas J. Gooßen

doi:10.1055/a-1648-2821

Synthesis, Table of Contents

Synthesis 2022; 54(03): 565-569
DOI: 10.1055/a-1648-2821

short review

Biaryl Synthesis via Electrooxidative Transition-Metal-Catalyzed C–H Activation

Authors

Jonas F. Goebel
Zhongyi Zeng∗
Lukas J. Gooßen∗

Abstract

All articles of this category

^‡ Evonik Chair of Organic Chemistry

Abstract

The use of electricity as an inexpensive and waste-free oxidant opens up new opportunities for the development of sustainable C–H functionalization reactions. Herein we summarize recent advances in the synthesis of biaryls through electrooxidative processes involving transition-metal-catalyzed ortho-directed C–H activation. A particular focus is set on electrooxidative C–H/C–M couplings and dehydrogenative couplings.

1 Introduction

2 Electrooxidative C–H/C–M Couplings

3 Electrooxidative C–H/C–H Couplings

4 Conclusion and Outlook

Key words

electrochemistry - C–H activation - directing groups - transition-metal catalysis - biaryls

Full Text

References

References
1 Franke R, Selent D, Börner A. Chem. Rev. 2012; 112: 5675
2 Okamoto K, Zhang J, Housekeeper JB, Marder SR, Luscombe CK. Macromolecules 2013; 46: 8059
3 von Nussbaum F, Brands M, Hinzen B, Weigand S, Häbich D. Angew. Chem. Int. Ed. 2006; 45: 5072
4 Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
5 Hiyama T. J. Organomet. Chem. 2002; 653: 58
6 Denmark SE, Sweis RF. Acc. Chem. Res. 2002; 35: 835
7 Tamao K, Sumitani K, Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
8 Milstein D, Stille JK. J. Am. Chem. Soc. 1978; 100: 3636
9 Negishi E. Acc. Chem. Res. 1982; 15: 340
10 Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062

11a Everson DA, Shrestha R, Weix DJ. J. Am. Chem. Soc. 2010; 132: 920
11b Knappke CE. I, Grupe S, Gartner D, Corpet M, Gosmini C, Jacobi von Wangelin A. Chem. Eur. J. 2014; 20: 6828
11c Everson DA, Weix DJ. J. Org. Chem. 2014; 79: 4793
11d Moragas T, Correa A, Martin R. Chem. Eur. J. 2014; 20: 8242
11e Kwa TL, Boelhouwer C. Tetrahedron 1969; 25: 5771
11f Amatore M, Gosmini C. Angew. Chem., Int. Ed. 2008; 47: 2089
11g Everson DA, Jones BA, Weix DJ. J. Am. Chem. Soc. 2012; 134: 6146

12 Giri R, Shi B.-F, Engle KM, Maugel N, Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242
13 Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
14 Waldvogel SR, Lips S, Selt M, Riehl B, Kampf CJ. Chem. Rev. 2018; 118: 6706
15 Wang H, Gao X, Lv Z, Abdelilah T, Lei A. Chem. Rev. 2019; 119: 6769
16 Li C.-J. Acc. Chem. Res. 2009; 42: 335
17 Li Z, Li C.-J. J. Am. Chem. Soc. 2004; 126: 11810
18 Malkowsky IM, Griesbach U, Pütter H, Waldvogel SR. Eur. J. Org. Chem. 2006; 2006: 4569
19 Malkowsky IM, Rommel CE, Fröhlich R, Griesbach U, Pütter H, Waldvogel SR. Chem. Eur. J. 2006; 12: 7482
20 Lam NY. S, Wu K, Yu J. Angew. Chem. Int. Ed. 2021; 60: 15767
21 Gandeepan P, Ackermann L. Chem 2018; 4: 199
22 Gong H, Zeng H, Zhou F, Li C.-J. Angew. Chem. Int. Ed. 2015; 54: 5718
23 Biafora A, Krause T, Hackenberger D, Belitz F, Gooßen LJ. Angew. Chem. Int. Ed. 2016; 55: 14752
24 Chiong HA, Pham Q.-N, Daugulis O. J. Am. Chem. Soc. 2007; 129: 9879
25 Ma C, Fang P, Mei T.-S. ACS Catal. 2018; 8: 7179
26 Sauermann N, Meyer TH, Qiu Y, Ackermann L. ACS Catal. 2018; 8: 7086
27 Qiu Y, Struwe J, Ackermann L. Synlett 2019; 30: 1164
28 Zhu C, Stangier M, Oliveira JC. A, Massignan L, Ackermann L. Chem. Eur. J. 2019; 25: 16382
29 Saito F, Aiso H, Kochi T, Kakiuchi F. Organomet. 2014; 33: 6704
30 Gooßen LJ, Rodríguez N, Linder C, Lange PP, Fromm A. ChemCatChem 2010; 2: 430
31 Gooßen LJ, Thiel WR, Rodríguez N, Linder C, Melzer B. Adv. Synth. Catal. 2007; 349: 2241
32 Cornella J, Righi M, Larrosa I. Angew. Chem. Int. Ed. 2011; 50: 9429
33 Zeng Z, Feceu A, Sivendran N, Gooßen LJ. Adv. Synth. Catal. 2021; 363: 2678
34 Goossen LJ, Deng G, Levy LM. Science 2006; 313: 662
35 Rodríguez N, Goossen LJ. Chem. Soc. Rev. 2011; 40: 5030
36 Zeng Z, Goebel JF, Liu X, Gooßen LJ. ACS Catal. 2021; 11: 6626