Issue 16, 2015

Unusual 1,2-aryl migration in Pd(ii)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines

Abstract

Inspired by the Hegedus aza-Wacker indole synthesis, we were intrigued with the fate of the aminopalladation intermediate if syn β-hydrogen is made inaccessible or unavailable. In contrast to our previously reported β-carbon elimination, cyclization of a variety of 2-alkenylaniline substrates under electrophilic palladium conditions unexpectedly afforded C3-substituted indoles. This unusual 1,2-migratory process was found to be operative across a variety of substrates with predictable migratory aptitude. A mechanistic proposal was put forward to rationalize the observed substrate dependence, and this unexpected finding could provide an opportunity for other related processes.

Graphical abstract: Unusual 1,2-aryl migration in Pd(ii)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines

Supplementary files

Article information

Article type
Communication
Submitted
23 Feb 2015
Accepted
12 Mar 2015
First published
12 Mar 2015

Org. Biomol. Chem., 2015,13, 4652-4656

Unusual 1,2-aryl migration in Pd(II)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines

S. W. Youn and S. R. Lee, Org. Biomol. Chem., 2015, 13, 4652 DOI: 10.1039/C5OB00361J

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