Photoinduced decarboxylative borylation of carboxylic acids

Alexander Fawcett, Johan Pradeilles, Yahui Wang, Tatsuya Mutsuga, Eddie L. Myers, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

249 Citations (Scopus)
584 Downloads (Pure)

Abstract

The conversion of widely available carboxylic acids into versatile boronic esters would be highly enabling for synthesis. Here we report that this transformation can be effected by illuminating the N-hydroxyphthalimide ester derivative of the carboxylic acid under visible light at room temperature in the presence of the diboron reagent, bis(catecholato)diboron. A simple workup allows isolation of the pinacol boronic ester. Experimental evidence suggests that boryl radical intermediates are involved in the process. The methodology is illustrated by the transformation of not just primary, secondary, and tertiary alkyl carboxylic acids but also a diverse range of natural product carboxylic acids, thereby demonstrating its broad utility and functional-group tolerance.

Original languageEnglish
Pages (from-to)283-286
Number of pages4
JournalScience
Volume357
Issue number6348
DOIs
Publication statusPublished - 21 Jul 2017

Fingerprint Dive into the research topics of 'Photoinduced decarboxylative borylation of carboxylic acids'. Together they form a unique fingerprint.

Cite this