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Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C-H Activation/Carbocyclization of Arylallenes.

ABSTRACT: Herein we report an example of tandem oxidative acetoxylation/carbocyclization of arylallenes 1 using Pd(OAc)2. The catalytic protocol is highly selective and provides access to new C-C and C-O bonds leading to a carbocyclization. The reaction proceeds via C-H activation by Pd. Mechanistic investigations show that the C-H activation is not the rate-limiting step and indicate that the reaction proceeds via acetoxylation of the allene.

SUBMITTER: Mazuela J

PROVIDER: S-EPMC4557776 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

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Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C-H Activation/Carbocyclization of Arylallenes.

Mazuela Javier J Banerjee Debasis D Bäckvall Jan-E JE

Journal of the American Chemical Society 20150728 30

Herein we report an example of tandem oxidative acetoxylation/carbocyclization of arylallenes 1 using Pd(OAc)2. The catalytic protocol is highly selective and provides access to new C-C and C-O bonds leading to a carbocyclization. The reaction proceeds via C-H activation by Pd. Mechanistic investigations show that the C-H activation is not the rate-limiting step and indicate that the reaction proceeds via acetoxylation of the allene. ...[more]

PMID: 26201012

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