title: Dual Hypervalent Iodine(III) Reagents and Photoredox Catalysis Enable Decarboxylative Ynonylation under Mild Conditions.
abstract: A combination of hypervalent iodine(III) reagents (HIR) and photoredox catalysis with visible light has enabled chemoselective decarboxylative ynonylation to construct ynones, ynamides, and ynoates. This ynonylation occurs effectively under mild reaction conditions at room temperature and on substrates with various sensitive and reactive functional groups. The reaction represents the first HIR/photoredox dual catalysis to form acyl radicals from α-ketoacids, followed by an unprecedented acyl radical addition to HIR-bound alkynes. Its efficient construction of an mGlu5 receptor inhibitor under neutral aqueous conditions suggests future visible-light-induced biological applications.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China).
authors.forename: Hanchu
authors.initials: H
authors.lastname: Huang
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China).
authors.forename: Guojin
authors.initials: G
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China). yiyunchen@sioc.ac.cn.
authors.forename: Yiyun
authors.initials: Y
authors.lastname: Chen
mesh_terms: D000215:Acylation; D000480:Alkynes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D006801:Humans; D007202:Indicators and Reagents; D007455:Iodine / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008027:Light; D010084:Oxidation-Reduction; D064529:Receptor, Metabotropic Glutamate 5 / Q000037:antagonists & inhibitors
chemical_list: D000480:Alkynes; D002264:Carboxylic Acids; D007202:Indicators and Reagents; D007659:Ketones; D064529:Receptor, Metabotropic Glutamate 5; D007455:Iodine
keywords: decarboxylation; homogeneous catalysis; hypervalent compounds; photochemistry; ynonylation