Metal-catalyzed reactions of organic nitriles and boronic acids to access diverse functionality

The nitrile or cyano (-CN) group is one of the most appreciated and effective functional groups in organic synthesis, having a polar unsaturated C-N triple bond. Despite sufficient stability and being intrinsically inert, the nitrile group can be easily transformed into many other functional groups,...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-06, Vol.2 (21), p.4243-4277
Main Authors: Dhara, Hirendra Nath, Rakshit, Amitava, Alam, Tipu, Patel, Bhisma K
Format: Article
Language:English
Subjects:
Acids
Amides
Amines
Carboxylic acids
Cascade chemical reactions
Chemical bonds
Chemical reactions
Chemical synthesis
Coupling (molecular)
Cross coupling
Cyanide
Cyano groups
Functional groups
Genotoxicity
Ketones
Low level
Metals
Nitriles
Transition metals
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Summary:The nitrile or cyano (-CN) group is one of the most appreciated and effective functional groups in organic synthesis, having a polar unsaturated C-N triple bond. Despite sufficient stability and being intrinsically inert, the nitrile group can be easily transformed into many other functional groups, such as amines, carboxylic acids, ketones, etc . which makes it a vital group in organic synthesis. On the other hand, despite several boronic acids having a low level of genotoxicity, they have found wide applicability in the field of organic synthesis, especially in transition metal-catalyzed cross-coupling reactions. Recently, transition-metal-catalyzed cascade additions or addition/cyclization processes of boronic acids to the nitrile group open up exciting and useful strategies to prepare a variety of functional molecules through the formation of C−C, C−N and C&z.dbd;O bonds. Boronic acids can be added to the cyano functionality through catalytic carbometallation or through a radical cascade process to provide newer pathways for the rapid construction of various important acyclic ketones or amides, carbamidines, carbocycles and N,O-heterocycles. The present review focuses on various transition-metal-catalyzed additions of boronic acids via carbometallation or radical cascade processes using the cyano group as an acceptor. This review summarises the latest reactions of boronic acids with functionalized nitriles in the presence of transition-metal catalysts.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00288d