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

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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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Article information


Submitted
05 Nov 2019
Accepted
09 Dec 2019
First published
12 Dec 2019

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

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

H. Huang, X. Wu, B. Leng, Y. Zhu, X. Meng, Y. Hong, B. Jiang and D. Wang, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01343A

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