Lewis acid catalyzed benzylic C-H bond functionalization of azaarenes: addition to enones

Hirotomo Komai; Tatsuhiko Yoshino; Shigeki Matsunaga; Motomu Kanai

doi:10.1021/ol200217y

Lewis acid catalyzed benzylic C-H bond functionalization of azaarenes: addition to enones

Org Lett. 2011 Apr 1;13(7):1706-9. doi: 10.1021/ol200217y. Epub 2011 Mar 3.

Authors

Hirotomo Komai¹, Tatsuhiko Yoshino, Shigeki Matsunaga, Motomu Kanai

Affiliation

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 21370873
DOI: 10.1021/ol200217y

Abstract

A Lewis acid catalyzed benzylic C-H bond functionalization of alkyl-substituted azaarenes is described. Sc(OTf)(3) and Y(OTf)(3) promoted the direct addition of alkyl-substituted azaarenes and benzoxazole to enones and an α,β-unsaturated N-acylpyrrole. Products were obtained in 60-96% yield.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aza Compounds / chemistry*
Benzene / chemistry*
Carbon / chemistry*
Catalysis
Hydrogen / chemistry*
Lewis Acids / chemistry*
Molecular Structure

Substances

Aza Compounds
Lewis Acids
Carbon
Hydrogen
Benzene