Premium
Highly Regioselective DABCO‐Catalyzed Nucleophilic Aromatic Substitution (S N Ar) Reaction of Methyl 2,6‐Dichloronicotinate with Phenols
Author(s) -
Shi YaoJun,
Humphrey Guy,
Maligres Peter E.,
Reamer Robert A.,
Williams J. Michael
Publication year - 2006
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.200505431
Subject(s) - dabco , chemistry , regioselectivity , pyridine , octane , phenols , triethylamine , medicinal chemistry , electrophilic aromatic substitution , nucleophile , nucleophilic aromatic substitution , catalysis , nucleophilic substitution , substitution reaction , adduct , organic chemistry
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 .