88112-02-1Relevant academic research and scientific papers
Development and Mechanistic Study of Quinoline-Directed Acyl C-O Bond Activation and Alkene Oxyacylation Reactions
Hoang, Giang T.,Walsh, Dylan J.,McGarry, Kathryn A.,Anderson, Constance B.,Douglas, Christopher J.
, p. 2972 - 2983 (2017/03/23)
The intramolecular addition of both an alkoxy and acyl substituent across an alkene, oxyacylation of alkenes, using rhodium catalyzed C-O bond activation of an 8-quinolinyl ester is described. Our unsuccessful attempts at intramolecular carboacylation of ketones via C-C bond activation ultimately informed our choice to pursue and develop the intramolecular oxyacylation of alkenes via quinoline-directed C-O bond activation. We provide a full account of our catalyst discovery, substrate scope, and mechanistic experiments for quinoline-directed alkene oxyacylation.
Photocyclization Reactions. Part 1. Synthesis of Dihydrobenzofuranols Using Photocyclization of 2-Alkoxybenzaldehydes, 2'-Alkoxyacetophenones, 2-Formylphenoxyacetic Acids and 2-Acetylphenoxyacetic Acids
Horaguchi, Takaaki,Tsukada, Chikara,Hasegawa, Eietsu,Shimizu, Takahachi,Suzuki, Tsuneo,Tanemura, Kiyoshi
, p. 1261 - 1272 (2007/10/02)
Photocyclization reactions were carried out on 2-alkoxybenzaldehydes 1a-f, 2'-alkoxyacetophenones 2a-h, 2-formylphenoxyacetic acids 1i-l and 2-acetylphenoxyacetic acids 2i-m.Irradiation opf 1a-f and 2a-h in acetonitrile gave the corresponding dihydrobenzofuranols 3, 5 and dihydroisobenzofuranols 4, 6.Using carboxylic acids 1i-l, 2i-m as starting materials, decarboxylation occurred immediately to give the corresponding ethers 1a-d, 2a-e.Further irradiation of the solution afforded dihydrobenzofuranols 3,5 and dihydroisobenzofuranols 4, 6.Substituent effects on photocyclization and reaction pathways are discussed.
