Copper‐Mediated Formation of Aryl, Heteroaryl, Vinyl and Alkynyl Difluoromethylphosphonates: A General Approach to Fluorinated Phosphate Mimics

• DOI: 10.1002/anie.201507130
• Publication Date: 2015-09-11T09:01:58Z
• Authors: Maria V. Ivanova; Alexandre Bayle; Tatiana Besset; Thomas Poisson; Xavier Pannecoucke
• Keywords: [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry; [CHIM.ORGA]Chemical Sciences/Organic chemistry; [CHIM.ANAL]Chemical Sciences/Analytical chemistry; [CHIM.CATA]Chemical Sciences/Catalysis; [CHIM.THER]Chemical Sciences/Medicinal Chemistry; 540; 01 natural sciences; [CHIM.CHEM]Chemical Sciences/Cheminformatics; 0104 chemical sciences

A general and efficient access to aryl, heteroaryl, vinyl alkynyl difluoromethylphosphonates is described. The developed methodology using TMSCF2PO(OEt)2, iodonium salts a copper salt provided straightforward manifold reach these highly relevant products. reaction proved be functional group tolerant proceeded under mild conditions, giving the corresponding products in good excellent yields. This method represents first synthetic route this important class of fluorinated scaffolds, which are well-recognized as vivo stable phosphate surrogates.