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Synthesis of 2-substituted indolines using sequential Pd-catalyzed processes

Lookup NU author(s): Herve Deboves, Christopher Hunter, Professor Richard Jackson

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Abstract

A concise route to enantiomerically pure 2-substituted indolines 4a-g and a 2-substituted tetrahydroquinoline 4h has been developed by application of the Pd-catalyzed coupling of amino functionalised organozinc reagents with 2-bromoiodobenzene, followed by Buchwald's palladium-catalyzed intramolecular amination reaction. The yields in the initial coupling are modest (36-52%), but the cyclisation yields are satisfactory (63-87%). The stereochemical integrity of a representative example was established by chiral phase HPLC.

Publication metadata

Author(s): Deboves HJC, Hunter C, Jackson RFW

Publication type: Article

Publication status: Published

Journal: Journal of the Royal Chemical Society: Perkin Transactions 1

Year: 2002

Issue: 6

Pages: 733-736

ISSN (print): 1472-7781

ISSN (electronic): 1364-5463

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/b200163b

DOI: 10.1039/b200163b

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