Transition-metal-free radical relay cyclization of vinyl azides with 1, 4-dihydropyridines involving a 1, 5-hydrogen-atom transfer: access to α-tetralone scaffolds. Issue 22 (12th October 2020)

• Record Type: Journal Article
• Authors: Liao, Yangzhen; Ran, Yu; Liu, Guijun; Liu, Peijun; Liu, Xiaozu
• Is Part Of: Organic chemistry frontiers. Volume 7:Issue 22(2020)
• Page Start: 3638
• Page End: 3647
• Publication Date: 2020-10-12
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d0qo01042a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The remote C(sp 3 )–H functionalization enabled by a radical-mediated 1, 5-hydrogen-atom transfer (HAT) process using vinyl azides and 1, 4-dihydropyridines as precursors has been described. Abstract : The remote C(sp 3 )–H functionalization enabled by a radical-mediated 1, 5-hydrogen-atom transfer (HAT) process using vinyl azides and 1, 4-dihydropyridines as precursors has been described. In this study, 1, 4-dihydropyridines can function as 1, 2-diradical synthons through sequential homolytic cleavage of an ipso -C–C bond and a β-C(sp 3 )–H bond. This reaction offers facile access to a diverse range of α-tetralones with excellent stereoselectivity. The utility of the present method is further highlighted by its application to rapid assembly of the tetracyclic scaffold present in furanosteroids as well as the synthesis of aromatic amines.