1. Excited-State Copper Catalysis for the Synthesis of Heterocycles
- Author
-
Christopher J. Johnson, Emmanuel A. Bazan Bergamino, Jagrut A. Shah, Arghya Banerjee, Nicoline C. Frederiks, Satavisha Sarkar, and Ming-Yu Ngai
- Subjects
Molecular Structure ,Chemistry ,Ligand ,Radical ,chemistry.chemical_element ,General Medicine ,General Chemistry ,Combinatorial chemistry ,Copper ,Catalysis ,Article ,chemistry.chemical_compound ,Heterocyclic Compounds ,Excited state ,Organometallic Compounds ,BINAP - Abstract
Heterocycles represent 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.
- Published
- 2021