Open AccessHighly Regioselective α-Chlorination of the BODIPY Chromophore with Copper(II) Chloride
Author(s) -
Xin Zhou,
Changjiang Yu,
Zeya Feng,
Yu Yang,
Jun Wang,
Erhong Hao,
Yun Wei,
Xiaolong Mu,
Lijuan Jiao
Publication year - 2015
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.5b02383
Subject(s) - regioselectivity , chemistry , halogenation , reagent , bodipy , chromophore , alkyl , chloride , aryl , combinatorial chemistry , organic chemistry , photochemistry , catalysis , fluorescence , physics , quantum mechanics
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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