Unusual 1,2-aryl migration in Pd(ii)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines.
Org Biomol Chem
; 13(16): 4652-6, 2015 Apr 28.
Article
em En
| MEDLINE
| ID: mdl-25793456
ABSTRACT
Inspired by the Hegedus aza-Wacker indole synthesis, we were intrigued with the fate of the aminopalladation intermediate if syn ß-hydrogen is made inaccessible or unavailable. In contrast to our previously reported ß-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.
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MEDLINE
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2015
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Article