Perfluoroalkyl Editing of Fluoroalkynes: Chemo-, Regio-, and Stereoselective Synthesis of (<i>E</i>)-(2-Amino-fluoroalkenyl)pyrimidines
Xiao-Ying Li, Ming-Yao Tang, Qian Tong, Danhua Ge, Mengtao Ma, Zhi‐Liang Shen, Xue‐Qiang Chu
Abstract
A chemo-, regio-, and stereoselective condensation reaction of perfluoroalkyl alkynes (PFAAs), (CH 2 O) n, and (NH 4 ) 2 CO 3 through the cleavage of five inert C(sp 3 )-F bonds at three distinct carbon sites, thereby establishing an unprecedented platform for synthesizing structurally unique ( E )-(2-amino-fluoroalkenyl)pyrimidines, is first developed. Remarkably, this reaction features mild reaction conditions, good compatibility with various functional groups, excellent E -stereoselectivity, late-stage modification of complex molecules, scalability, and versatile synthetic transformations of the resulting heterocyclic compounds.
Topics & Concepts
ChemistryStereoselectivityStereochemistryCombinatorial chemistryOrganic chemistryCatalysisFluorine in Organic ChemistrySynthesis and Biological EvaluationSynthesis and Reactions of Organic Compounds