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

A new catalytic approach for the synthesis of isochroman derivatives via direct C(sp(3))-H bond arylation is described. The oxidation reaction with [bis(trifluoroacetoxy)-iodo]benzene facilitates the regeneration of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in the C(sp(3))-H bond arylation of isochroman. The reaction conditions can also be used for alkyl Grignard reagents and amides to afford the corresponding isochroman derivatives.