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Published on: October 3, 2018
DDQ-catalyzed oxidative α-allylation of isochromans under aerobic conditions
Sujin Lee1,2, Sunhwa Jung1,2, Suyeon Hyeon1
1Department of Applied Chemistry, Hanyang University Ansan Gyeonggi-do 15588 Republic of Korea.
Abstract:
The allylation of isochromans at the α-position via aerobic DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) catalysis is described. This process involves the DDQ oxidation of various isochromans under mild conditions to generate oxocarbenium intermediates, which are effectively stabilized in equilibration in the presence of acid before undergoing allylation. Molecular oxygen and tert-butyl nitrite are employed as an environmentally benign oxidant and mediator, respectively, in the catalytic cycle. The transformation of an allylated product to biologically active molecules has also been successfully demonstrated.
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