An Olefinic 1, 2‐α‐Boryl Migration Enables 1, 2‐Bis(boronic esters) via Radical‐Polar Crossover Reaction. Issue 5 (4th January 2022)

• Record Type: Journal Article
• Authors: Zhang, Feng; Liao, Shangteng; Zhou, Lu; Yang, Kai; Wang, Chenglan; Lou, Yixian; Wang, Cece; Song, Qiuling
• Is Part Of: Chinese journal of chemistry. Volume 40:Issue 5(2022)
• Page Start: 582
• Page End: 588
• Publication Date: 2022-01-04
• Subjects: Borates -- Radical reactions -- 1, 2‐α‐Boryl migration -- Multicomponent reactions -- Diborylation; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202100701
• Languages: English
• ISSNs: 1001-604X

Abstract

Comprehensive Summary: A radical‐induced 1, 2‐ α ‐boryl migration through radical polar crossover reactions has been described. In this work, in situ formed vinyldiboron "ate" complexes from alkenyl Grignard reagent and diborylalkanes react with commercial radical precursors under light initiation. This three‐component process enables diborylation of alkene. This protocol features high atom economy, a broad substrate scope as well as good functional group toleration with mild conditions. Abstract : Radical‐polar crossover enables 1, 2‐bis(boronic esters) synthesis: A novel radical‐induced 1, 2‐ α ‐boryl migration of vinylboron "ate "complexes for 1, 2‐bis(boronic esters) synthesis was developed. This protocol features high atom economy, excellent functional group compatibility, broad substrate scope and mild conditions with diborylalkanes acting as boron source for diborylation.