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A Simple, Effective Boron‐Halide Ethoxylation Catalyst
Author(s) -
Moloy Kenneth G.
Publication year - 2010
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.201000004
Subject(s) - chemistry , nucleophile , boric acid , boron , iodide , halide , electrophile , bromide , catalysis , organic chemistry
Boron esters B(OR) 3 , readily derived from boric acid and alcohols, combine with iodide or bromide to catalyze the ethoxylation of alcohols and phenols, giving good rates and narrow product distributions. The combined action of a weak electrophile [B(OR) 3 ] and a weak nucleophile (halide) allows for the ethoxylation of base‐sensitive alcohols. Experiment suggests a new mechanism for this commercially important reaction proceeding through key β‐haloalkoxy intermediates.