4.8 Article

Selective Syntheses of Z-Alkenes via Photocatalyzed Decarboxylative Coupling of N-Hydroxyphthalimide Esters with Terminal Arylalkynes

Journal

ORGANIC LETTERS
Volume 21, Issue 7, Pages 2269-2272

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00558

Keywords

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Funding

  1. National Natural Science Foundation of China [21302231]
  2. Hunan Provincial Natural Science Foundation of China [14JJ3021]
  3. Programs Foundation of Ministry of Education of China [20130162120032]

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A novel, efficient Z-alkene synthesis via photo-catalyzed decarboxylative couplings between terminal aryl alkynes and alkyl N-hydroxyphthalimide (NHPI) esters, which are derived from aliphatic carboxylic acids, is described. A wide range of primary, secondary, and tertiary carboxylates as well as alpha-amino acid and alpha-oxyacid-derived esters were employed as suitable substrates. The mild reaction conditions, broad substrate scope, functional group tolerance, and operational simplicity make this decarboxylative coupling reaction a valuable method in organic syntheses.

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