Carboxamide-Accelerated Chemoselective Borylation of Iodoarenes under Photoirradiation

This study reports on the ortho-specific and chemoselective borylation of ortho-iodoarene possessing carboxamide under visible-light irradiation. When a haloarene containing both C–I and C–X bonds is employed as a substrate, another C–X bond (not ortho) remains intact during the reaction. Mechanistic studies revealed that the key to the success of this reaction is the generation of a diboron-bridged five-membered ring as a transition state, in which the diboron-bridged five-membered ring and the benzene ring in the transition state are perpendicular to each other, owing to steric repulsion by the iodine atom at the ortho position. This chemoselectivity is suitable for the synthesis of borylated building blocks. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synthesis - November 30, 2023 Category: Chemistry Authors: Nakashima, Yusei Sumimoto, Michinori Nishikata, Takashi Tags: paper Source Type: research