AUTHOR=Liu Baohua , Hu Qiong , Wen Yinshan , Fang Bo , Xu Xiaoliang , Hu Yimin 

TITLE=Versatile Dibenzothio[seleno]phenes via Hexadehydro-Diels–Alder Domino Cyclization

JOURNAL=Frontiers in Chemistry

VOLUME=7

YEAR=2019

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2019.00374

DOI=10.3389/fchem.2019.00374

ISSN=2296-2646

ABSTRACT=<p>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 played a pivotal role in constructing natural thio[seleno]phene cores, which were highly substituted, and is a robust method for producing fused heterocycles.</p>