Intramolecular Addition of Triarylmethanes to Alkynes Promoted by KOtBu/DMF: A Synthetic Approach to Indene Derivatives. Issue 3 (9th December 2015)

• Record Type: Journal Article
• Authors: Chen, Yan‐yan; Chen, Zhen‐yu; Zhang, Niu‐niu; Chen, Jia‐hua; Zhang, Xue‐jing; Yan, Ming
• Is Part Of: European journal of organic chemistry. Issue 3(2016)
• Page Start: 599
• Page End: 606
• Publication Date: 2015-12-09
• Subjects: Alkynes -- Intramolecular addition -- Radical reactions -- Triarylmethane -- Indene derivatives; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501356
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A method for the intramolecular addition of triarylmethanes to alkynes has been developed. The reaction was efficiently promoted by KO t Bu/DMF without any transition‐metal catalyst. A variety of indene derivatives were prepared in moderate to good yields. A cascade cyclization of 2‐alkyl‐substituted substrates at elevated reaction temperature gave bicyclic indene derivatives. The reaction is proposed to proceed through the generation of a triphenylmethyl radical. Abstract : Indene derivatives were prepared by the intramolecular addition of triarylmethanes to alkynes promoted by KO t Bu/DMF. A cascade cyclization of 2‐alkyl‐substituted substrates at elevated reaction temperature gave bicyclic indene derivatives. A free‐radical reaction mechanism is proposed.