Specific assembly of dihydrobenzofuran frameworks via Rh(iii)-catalysed C–H coupling of N-phenoxyacetamides with 2-alkenylphenols. (4th March 2022)

• Record Type: Journal Article
• Authors: Wei, Yinhui; Xu, Huiying; Chen, Fangyuan; Gao, Hui; Huang, Yugang; Yi, Wei; Zhou, Zhi
• Is Part Of: New journal of chemistry. Volume 46:Number 12(2022)
• Page Start: 5705
• Page End: 5711
• Publication Date: 2022-03-04
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d2nj00175f
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : The synergistic dual directing group-enabled and Rh(iii )-catalysed redox-neutral C–H functionalization/[3+2] annulation has been realized for the synthesis of dihydrobenzofurans. Abstract : The Rh(iii )-catalysed redox-neutral C–H coupling of N -phenoxyacetamides with 2-alkenylphenols has been developed, leading to the specific assembly of dihydrobenzofuran frameworks with good compatibility and profound synthetic utility. Integrated computational and experimental mechanistic studies revealed that the distinctive synergistic dual directing group-enabled unconventional reaction pathway involved a sequential intramolecular hydrogen transfer/nucleophilic 1, 4-addition process in which a five-membered rhodacycle and the cyclohexa-2, 4-dienone species might be used as the active intermediates.