Photo-mediated synthesis of halogenated spiro[4, 5]trienones of N-aryl alkynamides with PhI(OCOCF3)2 and KBr/KCl. Issue 10 (26th February 2020)

• Record Type: Journal Article
• Authors: Liu, Tong; Li, Yaming; Jiang, Linlin; Wang, Jiaao; Jin, Kun; Zhang, Rong; Duan, Chunying
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 10(2020)
• Page Start: 1933
• Page End: 1939
• Publication Date: 2020-02-26
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob00057d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A novel and convenient photo-mediated halogenated spirocyclization of N -( p -methoxyaryl)propiolamides has been developed. Abstract : A novel and convenient photo-mediated halogenated spirocyclization of N -( p -methoxyaryl)propiolamides has been developed. The photolysis of phenyliodine bis(trifluoroacetate) (PIFA) as an iodination reagent led to iodinated ipso -cyclization under the irradiation of a xenon lamp, while brominated ipso -cyclization or chlorinated ipso -cyclization was achieved by irradiating a mixture of PIFA and KBr/KCl under a blue LED. The present protocol simply utilizes light as the safe and clean energy source and doesn't require any external photocatalyst providing various 3-halospiro[4, 5]trienones in good to excellent yields (up to 93%).