Recent Advances in C–B Bond Formation through a Free Radical Pathway

The development of a methodology for the preparation of arylboronic acids or arylboronates is of significant interest to organic chemists. Classical synthetic methods to prepare these organoboron compounds are based on the reaction of Grignard or lithium reagents with trialkyl borates. In the past f...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 360; no. 6; pp. 1040 - 1053
Main Authors Yan, Guobing, Huang, Dayun, Wu, Xiangmei
Format Journal Article
LanguageEnglish
Published Heidelberg Wiley Subscription Services, Inc 20.03.2018
Subjects
Aromatic compounds
arylboronic esters
Borates
Boron
borylation
Chemical bonds
Chemists
Free radicals
Halides
Hydrocarbons
Lithium
Organoboron compounds
photoredox catalysts
Reaction mechanisms
Reagents
Transition metals
visible light
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Summary:The development of a methodology for the preparation of arylboronic acids or arylboronates is of significant interest to organic chemists. Classical synthetic methods to prepare these organoboron compounds are based on the reaction of Grignard or lithium reagents with trialkyl borates. In the past few decades, the transition‐ metal‐catalyzed borylation of aryl halides, or pseudohalides, and C–H bonds of hydrocarbons has been a powerful tool for the synthesis of arylboronates in modern organic synthesis. These transformations are generally considered to proceed via organometallic intermediates generated by oxidative addition or transmetalation processes from the boron reagent. Several reviews on this type of borylation catalyzed by transition metals have been published in the literature. Interestingly, there has been a novel recognition that the boron reagent can participate in free‐radical coupling via the homolytic cleavage of the boron‐boron bond in recent years. In this review, recent advances in this new area of boron chemistry are summarized and the reaction mechanisms are also discussed.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201701030