Boryl Radical Addition to Multiple Bonds in Organic Synthesis

• Published in: European journal of organic chemistry 2019-10, Vol.2019 (37), p.6308-6319
• Main Author: Taniguchi, Tsuyoshi
• Format: Article
• Language: English
• Subjects: Alkenes; Alkynes; Boranes; Boron; Carbonyl groups; Carbonyls; Chemical bonds; Chemical compounds; Chemical reactions; Cleavage; Hydrogen bonds; Multiple bonds; Organic chemistry; Organoboron compounds; Radical reactions; Radicals; Reaction mechanisms; Reagents; Synthetic methods
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201901010

Boryl radicals have recently contributed to the development of organoboron chemistry, but synthetic application of boryl radicals is still limited compared with other radical species. The recent development of new reagents and catalytic systems has expanded the practicality of boryl radicals in synthetic chemistry, and it has enabled addition reactions of boryl radicals to multiple bonds such as alkenes, alkynes, carbonyl groups and their derivatives. Boryl radical additions to multiple bonds can create not only novel organoboron compounds but also unusual chemical transformations. This review summarizes recently developed addition reactions of boryl radicals, which are roughly categorized by the strategy for formation of boryl radicals: (1) B–H bond cleavage and (2) B–B bond cleavage. Also, the reaction mechanism is outlined in order to understand the design and concept of each reaction. Recent advances in organoboron chemistry have enabled generation and reactions of boryl radicals in organic synthesis. This review summarizes addition reactions of boryl radicals to various multiple bonds, which offer easy access to novel organoboron compounds and useful chemical transformations.