Highly Regioselective α-Chlorination of the BODIPY Chromophore with Copper(II) Chloride

Organic Letters
Xin ZhouLijuan Jiao

Abstract

A general and efficient method for α-chlorination of 4,4'-difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) has been developed using CuCl2 as chlorination reagent. The reaction is characterized by complete 3/5-positions of BODIPY regioselectivity. This unusual highly regioselective α-halogenation of BODIPY is in sharp contrast to previously reported halogenation methods which preferred to occur first at the 2,6-positions of BODIPY. This approach provides a straightforward, facile, and economical route to 3- and/or 5-chloroBODIPYs with various meso-groups (H, alkyl, and aryl) and their derivatives.

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Citations

Oct 28, 2016·The Journal of Organic Chemistry·Jun WangLijuan Jiao
Jul 17, 2018·Chemistry, an Asian Journal·Madhurima PoddarRajneesh Misra
Jan 19, 2019·Chemical Communications : Chem Comm·Fan LvLijuan Jiao
Mar 19, 2020·Organic & Biomolecular Chemistry·Benjamin F HohlfeldArno Wiehe

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