Copper(I)/DDQ-Mediated Double-Dehydrogenative Diels-Alder Reaction of Aryl Butenes with 1,4-Diketones and Indolones

Wen-Lei Xu; Wei Hu; Wei-Ming Zhao; Min Wang; Jie Chen; Ling Zhou

doi:10.1021/acs.orglett.0c02486

Copper(I)/DDQ-Mediated Double-Dehydrogenative Diels-Alder Reaction of Aryl Butenes with 1,4-Diketones and Indolones

Org Lett. 2020 Sep 18;22(18):7169-7174. doi: 10.1021/acs.orglett.0c02486. Epub 2020 Sep 9.

Authors

Wen-Lei Xu¹, Wei Hu¹, Wei-Ming Zhao¹, Min Wang¹, Jie Chen¹, Ling Zhou¹

Affiliation

¹ Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, Department of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education, Northwest University, Xi'an 710127, P. R. China.

PMID: 32902298
DOI: 10.1021/acs.orglett.0c02486

Abstract

A copper(I)/DDQ-mediated double-dehydrogenative Diels-Alder (DDDA) reaction of simple butenes with 1,4-diketones and indolones has been established for the first time. This strategy is based on a tandem double-dehydrogenation/Diels-Alder reaction from nonprefunctionalized starting materials, in which both a diene and dienophile were in situ generated via activation of fourfold inert C(sp³)-H bonds in one catalytic system.