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Catalytic ?-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles.

ABSTRACT: A palladium N-heterocyclic carbene catalyzed methodology for the synthesis of substituted, N-unprotected indoles and azaindoles is reported. The protocol permits access to various, highly substituted members of these classes of compounds. Although two possible reaction pathways (deprotonative and Heck-like) can be proposed, control experiments, supported by computational studies, point toward a deprotonative mechanism being operative.

SUBMITTER: Marelli E 

PROVIDER: S-EPMC5745074 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature

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Catalytic α-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles.

Marelli Enrico E   Corpet Martin M   Minenkov Yury Y   Neyyappadath Rifahath M RM   Bismuto Alessandro A   Buccolini Giulia G   Curcio Massimiliano M   Cavallo Luigi L   Nolan Steven P SP  

ACS catalysis 20160330 5

A palladium N-heterocyclic carbene catalyzed methodology for the synthesis of substituted, N-unprotected indoles and azaindoles is reported. The protocol permits access to various, highly substituted members of these classes of compounds. Although two possible reaction pathways (deprotonative and Heck-like) can be proposed, control experiments, supported by computational studies, point toward a deprotonative mechanism being operative. ...[more]

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