Synthesis 2021; 53(18): 3151-3179
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

Sumon Basak
a   Department of Chemistry, Banaras Hindu University, Varanasi, UP 221005, India
,
Jyoti Prasad Biswas
b   Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, MH 400076, India
,
Debabrata Maiti
b   Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, MH 400076, India
› Author Affiliations
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



Publication 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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