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Palladium‐Catalyzed Aryl Amination–Heck Cyclization Cascade: A One‐Flask Approach to 3‐Substituted Indoles
Author(s) -
Jensen Thomas,
Pedersen Henrik,
BangAndersen Benny,
Madsen Robert,
Jørgensen Morten
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200703763
Subject(s) - amination , aryl , chemistry , ferrocene , allylic rearrangement , palladium , iodide , catalysis , combinatorial chemistry , indole test , organic chemistry , medicinal chemistry , alkyl , electrode , electrochemistry
Two for the price of one : A Pd/dppf‐based catalyst provides access to the title compounds from 1,2‐dihalogenated aromatic compounds and allylic amines in a single reaction flask. The initial aryl amination step occurs with excellent selectivity for the aryl iodide to ensure the formation of a single indole regioisomer, which can be functionalized in situ by N‐arylation (see scheme). dba=dibenzylideneacetone, dppf=1,1′‐bis(diphenylphospanyl)ferrocene.