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Borinic Acid‐Catalyzed Regioselective Ring‐Opening of 3,4‐ and 2,3‐Epoxy Alcohols with Halides
Author(s) -
Wang Grace,
Taylor Mark S.
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901268
Subject(s) - chemistry , regioselectivity , nucleophile , epoxide , ring (chemistry) , catalysis , halide , epoxy , sn2 reaction , polymer chemistry , nucleophilic substitution , medicinal chemistry , organic chemistry , stereochemistry
Methods for the regioselective ring‐opening of 3,4‐epoxy alcohols and 2,3‐epoxy alcohols with halide nucleophiles, using a diarylborinic acid catalyst, are disclosed. Ring‐opening occurs at the position proximal to the OH group, an effect ascribed to a catalytic tethering mechanism whereby coordination to the substrate OH group positions the diarylborinic acid to deliver a coordinated halide nucleophile. These methods provide access to halohydrin substitution patterns that were not previously accessible through catalytic epoxide ring‐opening reactions.