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Highly Regioselective DABCO-Catalyzed Nucleophilic Aromatic Substitution (SNAr) Reaction of Methyl 2,6-Dichloronicotinate with Phenols

✍ Scribed by Yao-Jun Shi; Guy Humphrey; Peter E. Maligres; Robert A. Reamer; J. Michael Williams

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 78 KB
Volume: 348
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.200505431

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✦ Synopsis

Abstract

Exclusive formation of 6‐aryloxy ethers 9 from an S~N~Ar reaction of methyl 2,6‐dichloronicotinate (2) with phenols 7 catalyzed by 1,4‐diazabicyclo[2.2.2]octane (DABCO) in the presence of stoichiometric triethylamine is described. The reaction proceeds via the regioselective formation of an unprecedented DABCO‐pyridine adduct 10a.

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