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. 2012 Jul 17;109(29):11605-8.
doi: 10.1073/pnas.1206532109. Epub 2012 Jul 2.

Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones

Timothy J Donohoe  1 , Ben S Pilgrim, Geraint R Jones, José A Bassuto
Affiliations

Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones

Timothy J Donohoe et al. Proc Natl Acad Sci U S A. .

Abstract

The utilization of sequential palladium-catalyzed α-arylation and cyclization reactions provides a general approach to an array of isoquinolines and their corresponding N-oxides. This methodology allows the convergent combination of readily available precursors in a regioselective manner and in excellent overall yields. This powerful route to polysubstituted isoquinolines, which is not limited to electron rich moieties, also allows rapid access to analogues of biologically active compounds.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1.
Scheme 1.
Retrosynthetic Strategy.
Scheme 2.
Scheme 2.
Exploring the scope of substituents R1, R3, and R4.
Scheme 3.
Scheme 3.
Exploring the scope of substituents R5, R6, R7, and R8.
Scheme 4.
Scheme 4.
A One-pot protocol.
Scheme 5.
Scheme 5.
Isoquinoline N-oxides.
Scheme 6.
Scheme 6.
Derivatizing estrone and androsterone.
See this image and copyright information in PMC

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