Organic Chemistry Portal

Abstracts

Search:

Radical Metal-Free Borylation of Aryl Iodides

Sandra Pinet*, Virginie Liautard, Mégane Debiais, Mathieu Pucheault *

*Institut des Sciences Moléculaires, UMR 5255 CNRS - Université de Bordeaux, Bordeaux-INP, 351 cours de la libération, 33405 Talence cedex, France, Email: sandra.pinetu-bordeaux.fr, mathieu.pucheaultu-bordeaux.fr

S. Pinet, V. Liautard, M. Debiais, M. Pucheault, Synthesis, 2017, 49, 4759-4768.

DOI: 10.1055/s-0036-1588431 (free Supporting Information)


see article for more reactions

Abstract

A simple metal-free borylation of aryl iodides is mediated by a fluoride sp2-sp3 diboron adduct. The reaction conditions tolerate various functional groups. Whereas electronic effects of substituents do not affect the borylation, steric hindrance does. The reaction proceeds via a radical mechanism in which pyridine stabilizes intermediate boryl radicals.

see article for more examples



Key Words

borylation, radical process, cesium fluoride, pyridine


ID: J66-Y2017