Cu(ii)-Catalyzed formal [4 + 2] cycloaddition between quinone methides (QMs) and electron-poor 3-vinylindoles?

Organic Chemistry Frontiers Pub Date: 2019-12-12 DOI: 10.1039/C9QO01343A

Abstract

A new Cu(II)-catalyzed formal [4 + 2] cycloaddition between quinone methides (QMs) including para-quinone methides (p-QMs) and ortho-quinone methides (o-QMs) and electron-poor 3-vinylindoles was established. A wide range of richly decorated indole-containing chromane derivatives were synthesized in acceptable yields and diastereoselectivity. Based on several control experiments, a possible mechanism was also proposed to elucidate the catalytic cycle pathway.

Graphical abstract: Cu(ii)-Catalyzed formal [4 + 2] cycloaddition between quinone methides (QMs) and electron-poor 3-vinylindoles
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