Hypervalent Iodine Reagents Enable Chemoselective Deboronative/Decarboxylative Alkenylation by Photoredox Catalysis1. Issue 6 (11th December 2014)

• Record Type: Journal Article
• Authors: Huang, Hanchu; Jia, Kunfang; Chen, Yiyun
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 6(2015)
• Page Start: 1881
• Page End: 1884
• Publication Date: 2014-12-11
• Subjects: alkenes -- chemoselectivity -- hypervalent compounds -- photochemistry -- ruthenium; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201410176
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : Good visibility : A visible‐light‐induced chemoselective deboronative/decarboxylative alkenylation is reported. This novel hypervalent‐iodine‐enabled radical reaction proceeds through a benziodoxole vinyl carboxylic acid intermediate (right). Aryl‐and acyl‐substituted alkenes containing sensitive functional groups are constructed in good yields. Alkyl = 1'‐, 2'‐, 3'‐alkyl, R = aryl, acyl.