4.8 Article

Simple and Direct sp3 C-H Bond Arylation of Tetrahydroisoquinolines and Isochromans via 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Oxidation under Mild Conditions

Journal

ORGANIC LETTERS
Volume 15, Issue 14, Pages 3650-3653

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol401534g

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, Japan

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The 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated sp(3) C-H bond arylation of tetrahydroisoquinolines and isochromans is described. The corresponding products were facilely synthesized via a simple nucleophilic addition reaction between readily available aryl Grignard reagents and iminium (or oxonium) cations generated in situ by DDQ oxidation of tetrahydroisoquinolines (or isochromans) under mild conditions.

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