Modular and Fast Synthesis of Versatile Secondary α,α-Dialkyl Boronates via Deoxygenative Alkylboration of Aldehydes

Wenhao Xu; Purui Zheng; Jun Zhou; Zihao Hu; Tao Xu

doi:10.1002/anie.202214213

Modular and Fast Synthesis of Versatile Secondary α,α-Dialkyl Boronates via Deoxygenative Alkylboration of Aldehydes

Angew Chem Int Ed Engl. 2022 Dec 5;61(49):e202214213. doi: 10.1002/anie.202214213. Epub 2022 Nov 3.

Authors

Wenhao Xu¹, Purui Zheng¹, Jun Zhou¹, Zihao Hu¹, Tao Xu¹

Affiliation

¹ Shanghai Key Laboratory of Chemical Assessment and Sustainability, School of Chemical Science and Engineering, Tongji University, 1239 Siping Road, Shanghai, 200092, P. R. China.

PMID: 36221813
DOI: 10.1002/anie.202214213

Abstract

Secondary α,α-dialkyl boronates are widely used due to their great versatility. Herein we report an unprecedented deoxygenative alkylboration of aldehydes, a facile method to access this type of products. A sequence of difunctionalization can be obtained smoothly from the readily available aldehydes in only two steps. This difunctionalization of aldehydes rather than conventional alkenes also opens new possibilities within the field.

Keywords: Aldehydes; Alkylboration; Metallaphotoredox; Reductive Cross-Coupling; Relay Catalysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes*
Alkenes*
Catalysis
Molecular Structure
Stereoisomerism

Substances

Aldehydes
Alkenes