Palladium‐Catalyzed Aryl Amination–Heck Cyclization Cascade: A One‐Flask Approach to 3‐Substituted Indoles | Zendy

Jensen Thomas | Zendy; Pedersen Henrik | Zendy; BangAndersen Benny | Zendy; Madsen Robert | Zendy; Jørgensen Morten | Zendy

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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.

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