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

Title
Unusual 1,2-aryl migration in Pd(II)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines
Author
윤소원
Keywords
C-H AMINATION; PALLADIUM-CATALYZED REACTIONS; BETA-HYDRIDE ELIMINATION; INDOLE SYNTHESIS; INTERNAL ALKYNES; REGIOCONTROLLED SYNTHESIS; 4-SUBSTITUTED INDOLES; SUBSTITUTED INDOLES; COUPLING REACTIONS; CUPRIC CHLORIDE
Issue Date
2015-04
Publisher
ROYAL SOC CHEMISTRY
Citation
ORGANIC & BIOMOLECULAR CHEMISTRY, v. 13, NO 16, Page. 4652-4656
Abstract
Inspired by the Hegedus aza-Wacker indole synthesis, we were intrigued with the fate of the aminopalladation intermediate if syn mu-hydrogen is made inaccessible or unavailable. In contrast to our previously reported beta-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.
URI
http://pubs.rsc.org/en/Content/ArticleLanding/2015/OB/C5OB00361J#!divAbstracthttp://hdl.handle.net/20.500.11754/23717
ISSN
1477-0520; 1477-0539
DOI
10.1039/c5ob00361j
Appears in Collections:
COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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