Transition-metal-free C–C bond forming reactions of aryl, alkenyl and alkynylboronic acids and their derivatives

Literature Information

Publication Date 2014-09-03
DOI 10.1039/C4CS00195H
Impact Factor 54.564
Authors

S. Roscales, A. G. Csákÿ


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Abstract

Investigation of new methods for the synthesis of C–C bonds is fundamental for the development of new organic drugs and materials. Aryl-, alkenyl- and alkynylboronic acids and their derivatives constitute attractive reagents towards this end, due to their stability, low toxicity and ease of handling. However, these compounds are only moderately nucleophilic. Consequently, the most popular C–C bond forming reactions of these boronic acids, such as the Suzuki–Miyaura, Heck, and Hayashi–Miyaura reactions, or additions to CO and CN bonds, require catalysis by transition metals. However, due to the toxicity and cost of transition metals, some new methods for C–C bond formation using aryl-, alkenyl- and alkynylboronic acids under transition-metal-free conditions are beginning to emerge. In this tutorial review, the recent synthetic advances in this field are highlighted and discussed.

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Chemical Society Reviews

Chemical Society Reviews
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Chem Soc Rev publishes review articles covering important topics at the forefront of the chemical sciences. Reviews should be of the very highest quality and international impact. We particularly encourage international and multidisciplinary collaborations among our authors. Our scope covers the breadth of the chemical sciences, including interdisciplinary topics where the article has a basis in chemistry. Topics include: Analytical chemistry Biomaterials chemistry Bioorganic/medicinal chemistry Catalysis Chemical Biology Coordination Chemistry Crystal Engineering Energy Sustainable chemistry Green chemistry Inorganic chemistry Inorganic materials Main group chemistry Nanoscience Organic chemistry Organic materials Organometallics Physical chemistry Supramolecular chemistry Synthetic methodology Theoretical and computational chemistry

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