Addition of N-Heterocyclic Carbenes to Imines: Phenoxide Assisted Deprotonation of an Imidazolium Moiety and Generation of Breslow Intermediates Derived from Imines

TY - JOUR

T1 - Addition of N-Heterocyclic Carbenes to Imines: Phenoxide Assisted Deprotonation of an Imidazolium Moiety and Generation of Breslow Intermediates Derived from Imines

AU - Simonovic, Stevan

AU - Frison, Jean-Cedric

AU - Koyuncu, Hasan

AU - Whitwood, Adrian C.

AU - Douthwaite, Richard E.

PY - 2009/1/1

Y1 - 2009/1/1

N2 - Reactions between imidazolium-imine salts and base result in C-C bond formation via Intermediate N-heterocyclic carbenes. In the presence of a proximal OH moiety, carbene formation occurs via Intramolecular deprotonation by phenoxide. For simple imines, a reactive Breslow-type intermediate gives access to new heterocycles with the formation of six- and seven-member rings.

AB - Reactions between imidazolium-imine salts and base result in C-C bond formation via Intermediate N-heterocyclic carbenes. In the presence of a proximal OH moiety, carbene formation occurs via Intramolecular deprotonation by phenoxide. For simple imines, a reactive Breslow-type intermediate gives access to new heterocycles with the formation of six- and seven-member rings.

KW - NUCLEAR MAGNETIC-RESONANCE

KW - C-H ACTIVATION

KW - DIRECT ANNULATIONS

KW - STABLE CARBENE

KW - ENALS

KW - BOND

KW - DERIVATIVES

KW - MECHANISM

KW - HYDROGEN

KW - LACTAMS

UR - http://www.scopus.com/inward/record.url?scp=59649118413&partnerID=8YFLogxK

U2 - 10.1021/ol802572n

DO - 10.1021/ol802572n

M3 - Article

SN - 1523-7060

VL - 11

SP - 245

EP - 247

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -