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CC BY-NC-ND 4.0 · Synthesis 2023; 55(01): 1-26
DOI: 10.1055/a-1939-7052
DOI: 10.1055/a-1939-7052
review
Recent Advances in Room-Temperature Direct C–H Arylation Methodologies
Financial support from the Okinawa Institute of Science and Technology Graduate University is gratefully acknowledged.
Abstract
In recent decades, direct C–H arylation has become a preferred tool for biaryl coupling over traditional cross-coupling methods owing to its operationally simple protocol, inherent atom and step economy, and reduced metallic waste. Several elegant methods have been developed that offer the facile transformation of usually inert Csp2–H bonds into Csp2–Csp2 bonds in a single synthetic operation. Despite many merits, a major drawback to this chemistry comes from the low reactivity of aryl C–H bonds, which often mandate harsh reaction conditions compromising sustainability. Hence, developing reaction protocols that require milder conditions has become an important goal in this area of research. This review article comprehensively highlights the synthesis and mechanistic aspects of direct C–H arylation reactions, which proceed at or below room temperature.
1 Introduction
2 Concepts and Examples
2.1 Transition-Metal-Catalyzed Procedures
2.1.1 Pd Catalysis
2.1.2 Other Metal-Based Procedures
2.1.3 Additive-Free Procedures
2.2 Direct Arylation Polymerization
2.3 Photocatalyzed Procedures
2.3.1 Organometallic C–H-Activation-Based Procedures
2.3.2 Radical-Addition-Based Procedures
2.4 Transition-Metal-Free Procedures
2.4.1 Base-Mediated Procedures
2.4.2 Iodonium- and Diazonium-Salt-Based Procedures
2.5 Electrocatalyzed Procedures
3 Summary and Outlook
Keywords
direct C–H arylation - mild reaction conditions - room temperature - transition-metal-catalyzed - photocatalyzed - electrocatalyzedPublikationsverlauf
Eingereicht: 30. Juni 2022
Angenommen nach Revision: 23. August 2022
Accepted Manuscript online:
08. September 2022
Artikel online veröffentlicht:
20. Oktober 2022
© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
Georg Thieme Verlag KG
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