Organocatalytic Approach for C(sp³)-H Bond Arylation, Alkylation, and Amidation of Isochromans under Facile Conditions

Wataru Muramatsu* and Kimihiro Nakano

*Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki, Nagasaki 852-8521, Japan, Email: muramatunagasaki-u.ac.jp

W. Muramatsu, K. Nakano, Org. Lett., 2014, 16, 2042-2045.

DOI: 10.1021/ol5006399

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Abstract

The use of [bis(trifluoroacetoxy)iodo]benzene as stoichiometric oxidant and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone as organocatalyst enables a convenient oxidation of isochromans. A further reaction with grignard reagents or amides affords the corresponding isochroman derivatives.

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Key Words

Isochromans, PIFA, DDQ, Organocatalysis

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ID: J54-Y2014