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Oxidative Arylation of Isochroman

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Soo J. Park†, Jason R. Price‡, and Matthew H. Todd*†

^†School of Chemistry and ^‡Crystal Structure Analysis Facility, School of Chemistry, The University of Sydney, NSW 2006, Australia

J. Org. Chem., 2012, 77 (2), pp 949–955

DOI: 10.1021/jo2021373

Publication Date (Web): December 5, 2011

*E-mail: matthew.todd@sydney.edu.au.

Section:

Heterocyclic Compounds (One Hetero Atom)

Abstract

We report the use of a previously intractable nucleophile, anisole, in an oxidative “cross-dehydrogenative coupling” (CDC) reaction with the cyclic ether isochroman, as well as derivatives of both components. Metal catalysis was required for the reaction to proceed efficiently, and the reaction is highly sensitive to modification of either coupling partner but is able to produce a range of novel compounds via what is a synthetic alternative to the traditional oxa-Pictet–Spengler reaction.

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History

Published In Issue January 20, 2012
Article ASAPDecember 29, 2011
Just Accepted ManuscriptDecember 05, 2011
Received: October 15, 2011

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Oxidative Arylation of Isochroman

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Related Content

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Iridium-Catalyzed [2+2+2] Cycloaddition of α,ω-Diynes with Isocyanates

An Enantioselective Approach toward 3,4-Dihydroisocoumarin through the Bromocyclization of Styrene-type Carboxylic Acids

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