Excited‐State Copper Catalysis for the Synthesis of Heterocycles. (7th December 2021)

• Record Type: Journal Article
• Authors: Banerjee, Arghya; Sarkar, Satavisha; Shah, Jagrut A.; Frederiks, Nicoline C.; Bazan‐Bergamino, Emmanuel A.; Johnson, Christopher J.; Ngai, Ming‐Yu
• Is Part Of: Angewandte Chemie. Volume 134:Number 4(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2021-12-07
• Subjects: aroylation -- copper catalysis -- heterocycles -- photoredox -- radicals; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202113841
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Heterocycles are one of the largest groups of organic moieties with significant medicinal, chemical, and industrial applications. Herein, we report the discovery and development of visible‐light‐induced, synergistic excited‐state copper catalysis using a combination of Cu(IPr)I as a catalyst and rac ‐BINAP as a ligand, which produces more than 10 distinct classes of heterocycles. The reaction tolerates a broad array of functional groups and complex molecular scaffolds, including derivatives of peptides, natural products, and marketed drugs. Preliminary mechanistic investigation suggests in situ generations of [Cu(BINAP)2 ] + and [Cu(IPr)2 ] + catalysts that work cooperatively under visible‐light irradiation to facilitate catalytic carbo‐aroylation of unactivated alkenes, affording a wide range of useful heterocycles. Abstract : Visible‐light‐induced excited‐state copper catalysis enables the synthesis of more than 10 distinct classes of heterocycles. The reaction tolerates a broad array of functional groups and complex molecular scaffolds, including derivatives of peptides, natural products, and marketed drugs.