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- Title
Cyclocarbonylative Sonogashira Reactions of 1-Ethynylbenzyl Alcohols: Synthesis of 1-Carbonylmethylene-1,3-Dihydroisobenzofurans.
- Authors
Aronica, Laura Antonella; Giannotti, Luca; Tuci, Giulia; Zinna, Francesco
- Abstract
In this work, we present a carbonylative Sonogashira reaction of o-ethynyl benzyl alcohols and aryl iodides, followed by a cyclization process to selectively give carbonylmethylene isobenzofurans in high yields and in an atom-economic fashion. The reaction can be carried out in the absence of CuI, with a small amount of PdCl2(PPh3)2 (0.2-0.5 mol-%), using aryl iodides bearing both electron-withdrawing and electron-donating groups. Of the two possible stereoisomeric products, Z-isobenzofuran derivatives were obtained as major products. But, when the reaction was extended to a secondary alcohol, an interesting switch in stereoselectivity was observed.
- Subjects
BENZYL alcohol; ARYL iodides; SONOGASHIRA reaction; RING formation (Chemistry); CARBONYL compounds; ISOBENZOFURAN; STEREOISOMERS; STEREOSELECTIVE reactions
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 22, p4944
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500539