Synthesis of β-Difluoroalkylated Acrylonitriles in the Presence of Copper Powder.
A highly regio- and stereoselective copper-mediated cyanodifluoroalkylation of alkynes with ethyl difluoroiodoacetate and trimethylsilyl cyanide (TMSCN) is described. The three-component coupling reaction provides straightforward access to a variety of useful difluoroalkyl-substituted acrylonitriles. The introduction of the nitrile unit is of great importance in drug discovery for the modification of this fragment. Preliminary mechanistic investigations indicate that a vinyl iodide intermediate and a difluoroalkyl radical might be involved in this transformation.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, P. R. China.
Yu-Tao
YT
He
State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, P. R. China.
Lian-Hua
LH
Li
State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, P. R. China.
Qiang
Q
Wang
Radiochemistry Laboratory, School of Nuclear Science and Technology, Lanzhou University , Lanzhou 730000, P. R. China.
Wangsuo
W
Wu
State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, P. R. China.|State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Science , Lanzhou, 730000, P. R. China.
Yong-Min
YM
Liang