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A One-Pot Double C–H Activation Palladium Catalyzed Route to a Unique Class of Highly Functionalized Thienoisoquinolines

Author:
Wong, Nicholas W. Y., Forgione, Pat
Source:
Organic letters 2012 v.14 no.11 pp. 2738-2741
ISSN:
1523-7052
Subject:
carbon-hydrogen bond activation, catalytic activity, chemical reactions, chemical structure, organic compounds, palladium, regioselectivity
Abstract:
The synthesis of a unique class of highly functionalized 3,4-thienoisoquinolines via an efficient palladium-catalyzed one-pot, regioselective double C–H activation is presented. This class of biologically relevant compounds has been prepared in five steps from commercially available starting materials with overall yields ranging from 27 to 62%. A masked carboxylic acid was used to direct C–H activation to the typically less reactive C4 position. Additionally, the carboxylic acid provides a synthetically useful handle for further functionalization.
Agid:
5783850