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Synthesis 2021; 53(18): 3151-3179
DOI: 10.1055/a-1485-4666
DOI: 10.1055/a-1485-4666
special topic
Bond Activation – in Honor of Prof. Shinji Murai
Transition-Metal-Catalyzed C–H Arylation Using Organoboron Reagents
This activity is supported by Science and Engineering Research Board (SERB), India (CRG/2018/003915). Financial support has been received from Council of Scientific and Industrial Research, India (CSIR-India) by J.P.B.
Abstract
Aryl rings are ubiquitous in the core of numerous natural product and industrially important molecules and thus their facile synthesis is of major interest in the scientific community and industry. Although multiple strategies enable access to these skeletons, metal-catalyzed C–H activation is promising due to its remarkable efficiency. Commercially available organoboron reagents, a prominent arylating partner in the cross-coupling domain, have also been utilized for direct arylation. Organoborons are bench-stable, inexpensive, and readily available coupling partners that promise regioselectivity, chemodivergence, cost-efficiency, and atom-economy without requiring harsh and forcing conditions. This critical, short review presents a summary of all major studies of arylation using organoborons in transition-metal catalysis since 2005.
1 Introduction
2 Arylation without Directing Group Assistance
2.1 Palladium Catalysis
2.2 Iron Catalysis
2.3 Gold Catalysis
3 Arylation with Directing Group Assistance
3.1 Palladium Catalysis
3.2 Ruthenium Catalysis
3.3 Rhodium Catalysis
3.4 Nickel Catalysis
3.5 Cobalt Catalysis
3.6 Copper Catalysis
4 Conclusion
Key words
transition-metal catalysis - C–H activation - arylation - organoboron - C–H functionalization - heterocyclePublication History
Received: 15 March 2021
Accepted after revision: 19 April 2021
Accepted Manuscript online:
19 April 2021
Article published online:
02 June 2021
© 2021. Thieme. All rights reserved
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Alkylarene synthesis by C−H activation, see reviews:
Alkenylarene synthesis by C−H activation, see reviews:
Biaryl synthesis by C−H activation, see reviews:
For reviews on metal-mediated arylation, see: