N-heterocyclic carbene catalyzed intramolecular acylation of allylic electrophiles.
The N-heterocyclic carbene (NHC) catalyzed addition reaction has been well documented recently; however, the NHC-catalyzed substitution reaction especially the SN2' type reaction remains a challenge. As one of the most fundamental reaction types in organic chemistry, the SN2' reaction catalyzed by NHC would be a powerful tool in organic synthesis. Therefore, the first NHC-catalyzed intramolecular SN2' substitution reaction of aldehyde with allylic electrophiles has been developed. A variety of α,β-unsaturated chromanones were obtained under a domino SN2' reaction and isomerization. Mechanistic experiments were conducted to confirm the nature of this SN2' reaction.
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University , Xi'an 710069, P. R. China.
Ming
M
Zhao
Hui
H
Yang
Miao-Miao
MM
Li
Jie
J
Chen
Ling
L
Zhou