Assembly of tetracyclic tetrahydrocarbazoles via a visible-light promoted cascade process. Issue 9 (30th March 2022)

• Record Type: Journal Article
• Authors: Mei, Haibo; Yu, Yingjie; Wang, Chengting; Liu, Aiyao; Han, Jianlin
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 9(2022)
• Page Start: 2516
• Page End: 2521
• Publication Date: 2022-03-30
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00247g
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A photocatalytic cascade reaction of alkene tethered indoles and bromodifluoroacetate esters has been developed, which provides a novel access to tetracyclic tetrahydrocarbazole derivatives. Abstract : We disclose an efficient method for the synthesis of tetracyclic tetrahydrocarbazoles via a visible-light promoted cascade reaction of alkene tethered indoles and bromodifluoroacetate esters. This reaction involves the formation of two C–C bonds and one C–N bond and proceeds via a key reactive tetrahydrocarbazole intermediate and dual cyclization. The reaction features mild conditions, wide substrate scope, and good chemical yields, and provides a new strategy for the synthesis of tetracyclic tetrahydrocarbazole derivatives. The synthetic utility of this reaction was further demonstrated by the large-scale synthesis and reduction of the obtained tetracyclic tetrahydrocarbazole product.