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Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones

Authors :
Zihang Qiu
Jianbin Li
Chao-Jun Li
Haining Wang
Chia-Yu Huang
Source :
Journal of the American Chemical Society. 142(30)
Publication Year :
2020

Abstract

Direct conversion of aldehydes and ketones into alkylboronic esters via deoxygenative borylation represents an unknown yet highly desirable transformation. Herein, we present a one-step and metal-free method for carbonyl deoxy-borylation under mild conditions. A wide range of aromatic aldehydes and ketones are tolerated and successfully converted into the corresponding benzylboronates. By the same deoxygenation manifold with aliphatic aldehydes and ketones, we also enable a concise synthesis of 1,1,2-tris(boronates), a family of compounds that currently lack efficient synthetic methods. Given its simplicity and versatility, we expect that this novel borylation approach could show great promise in organoboron synthesis and inspire more carbonyl deoxygenative transformations in both academic and industrial settings.

Details

ISSN :
15205126
Volume :
142
Issue :
30
Database :
OpenAIRE
Journal :
Journal of the American Chemical Society
Accession number :
edsair.doi.dedup.....12fbf41661a307dec022b9f63a719e56