Rhodium(i)-catalysed cycloisomerisation/6π electrocyclisation of 5-(ethynylamino)pent-2-yn-1-yl esters to 2, 3-dihydrobenzo[f]indoles. (27th June 2022)

• Record Type: Journal Article
• Authors: Merrett, James Theodore; Chen, Xiaoyu; Kyne, Sara Helen; Harode, Mandeep; Chan, Philip Wai Hong
• Is Part Of: New journal of chemistry. Volume 46:Number 28(2022)
• Page Start: 13519
• Page End: 13523
• Publication Date: 2022-06-27
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d2nj01992b
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : A rare instance in rhodium catalysis of an in situ formed rhodacycle that undergoes a formal 1, 8-acyloxy migration-initiated reductive elimination. Abstract : A synthetic method to prepare 2, 3-dihydro-1 H -benzo[ f ]indoles that relies on the rhodium(i )-catalysed cycloisomerisation/6π electrocyclisation of 5-(ethylnylamino)pent-2-yn-1-yl esters is described. The reaction mechanism was delineated to involve a rare instance in rhodium catalysis of an in situ formed rhodacycle that is susceptible to a formal 1, 8-acyloxy migration-initiated reductive elimination. This is followed by the proposed ensuing 1, 4-allenene undergoing a 6π electrocyclisation to give the N -heterocyclic product.