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Versatile Dibenzothio[seleno]phenes via Hexadehydro-Diels-Alder Domino Cyclization.

ABSTRACT: A facile strategy to synthesize highly substituted dibenzoselenophenes and dibenzothiophenes by a domino hexadehydro-Diels-Alder reaction is reported in this article. The formation of three new C-C bonds, one new Caryl-Se/Caryl-S bond, and C-H ?-bond migration via one-pot multiterminal cycloaddition reactions were involved in over three transformations. The target tetracyclic compounds were prepared from tetraynes with a triphenylphosphine selenide or triphenylphosphine sulfide. This reaction played a pivotal role in constructing natural thio[seleno]phene cores, which were highly substituted, and is a robust method for producing fused heterocycles.

SUBMITTER: Liu B

PROVIDER: S-EPMC6543197 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Versatile Dibenzothio[seleno]phenes via Hexadehydro-Diels-Alder Domino Cyclization.

Liu Baohua B Hu Qiong Q Wen Yinshan Y Fang Bo B Xu Xiaoliang X Hu Yimin Y

Frontiers in chemistry 20190524

A facile strategy to synthesize highly substituted dibenzoselenophenes and dibenzothiophenes by a domino hexadehydro-Diels-Alder reaction is reported in this article. The formation of three new C-C bonds, one new Caryl-Se/Caryl-S bond, and C-H σ-bond migration via one-pot multiterminal cycloaddition reactions were involved in over three transformations. The target tetracyclic compounds were prepared from tetraynes with a triphenylphosphine selenide or triphenylphosphine sulfide. This reaction pl ...[more]

PMID: 31179274

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