Highly Regioselective DABCO‐Catalyzed Nucleophilic Aromatic Substitution (S N Ar) Reaction of Methyl 2,6‐Dichloronicotinate with Phenols | Zendy

Shi YaoJun | Zendy; Humphrey Guy | Zendy; Maligres Peter E. | Zendy; Reamer Robert A. | Zendy; Williams J. Michael | Zendy

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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 .

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