title: Hypervalent iodine reagents enable chemoselective deboronative/decarboxylative alkenylation by photoredox catalysis.
abstract: Chemoselective C(sp(3))-C(sp(2)) coupling reactions under mild reaction conditions are useful for synthesizing alkyl-substituted alkenes having sensitive functional groups. Reported here is a visible-light-induced chemoselective alkenylation through a deboronation/decarboxylation sequence under neutral aqueous reaction conditions at room temperature. This reaction represents the first hypervalent-iodine-enabled radical decarboxylative alkenylation reaction, and a novel benziodoxole-vinyl carboxylic acid reaction intermediate was isolated. This C(sp(3))-C(sp(2)) coupling reaction leads to aryl-and acyl-substituted alkenes containing various sensitive functional groups. The excellent chemoselectivity, stable reactants, and neutral aqueous reaction conditions of the reaction suggest future biomolecule applications.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, 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.forename: Kunfang
authors.initials: K
authors.lastname: Jia
authors.forename: Yiyun
authors.initials: Y
authors.lastname: Chen
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007202:Indicators and Reagents / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D010084:Oxidation-Reduction; D055668:Photochemical Processes
chemical_list: D000475:Alkenes; D007202:Indicators and Reagents; D007455:Iodine
keywords: alkenes; chemoselectivity; hypervalent compounds; photochemistry; ruthenium