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Synthesis of benzothiophene and indole derivatives through metal-free propargyl-allene rearrangement and allyl migration.

ABSTRACT: An efficient base-catalyzed protocol for the synthesis of benzothiophene is described. The reaction proceeds via base-promoted propargyl-allenyl rearrangement followed by cyclization and allyl migration. Phosphine-substituted indoles can be synthesized by a similar strategy.

SUBMITTER: Yao J 

PROVIDER: S-EPMC5629416 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Synthesis of benzothiophene and indole derivatives through metal-free propargyl-allene rearrangement and allyl migration.

Yao Jinzhong J   Xie Yajie Y   Zhang Lianpeng L   Li Yujin Y   Zhou Hongwei H  

Beilstein journal of organic chemistry 20170906

An efficient base-catalyzed protocol for the synthesis of benzothiophene is described. The reaction proceeds via base-promoted propargyl-allenyl rearrangement followed by cyclization and allyl migration. Phosphine-substituted indoles can be synthesized by a similar strategy. ...[more]

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