Pd‐Catalyzed Selective Carbonylation of gem‐Difluoroalkenes: A Practical Synthesis of Difluoromethylated Esters. Issue 14 (3rd March 2019)

• Record Type: Journal Article
• Authors: Liu, Jiawang; Yang, Ji; Ferretti, Francesco; Jackstell, Ralf; Beller, Matthias
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 14(2019)
• Page Start: 4690
• Page End: 4694
• Publication Date: 2019-03-03
• Subjects: carbonylation -- difluoromethylated esters -- fluoroalkenes -- palladium -- selectivity; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201813801
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The first catalyst for the alkoxycarbonylation of gem ‐difluoroalkenes is described. This novel catalytic transformation proceeds in the presence of Pd(acac)2 /1, 2‐bis((di‐ tert ‐butylphosphan‐yl)methyl)benzene (btbpx) (L4 ) and allows for an efficient and straightforward access to a range of difluoromethylated esters in high yields and regioselectivities. The synthetic utility of the protocol is showcased in the practical synthesis of a Cyclandelate analogue using this methodology as the key step. Abstract : The first selective carbonylation of gem ‐difluoroalkenes was developed, providing a general approach to a variety of synthetically useful difluoromethylated esters in high yields and excellent regioselectivities.