96547-44-3Relevant academic research and scientific papers
Copper-Catalyzed Silylcupration of Activated Alkynes
Vercruysse, Sébastien,Jouvin, Kévin,Riant, Olivier,Evano, Gwilherm
, p. 3373 - 3381 (2016/09/12)
A highly efficient catalytic silylcupration of activated alkynes is reported. Upon reaction with silylboronates and methanol in THF at room temperature in the presence of copper(I) fluoride tris(triphenylphosphine), a range of ynamides and propiolates were found to undergo a smooth silylcupration. This reaction, which tolerates various functional groups, affords a straightforward and efficient entry to the corresponding β-silylenamides and -acrylates, which were formed with high levels of regio- and stereoselectivities.
P[N(i-Bu)CH2CH2]3N: Nonionic Lewis base for promoting the room-temperature synthesis of α,β-unsaturated esters, fluorides, ketones, and nitriles using Wadsworth - Emmons phosphonates
Chintareddy, Venkat Reddy,Ellern, Arkady,Verkade, John G.
supporting information; experimental part, p. 7166 - 7174 (2010/12/25)
The bicyclic triaminophosphine P(RNCH2CH2) 3N (R = i-Bu, 1c) serves as an effective promoter for the room-temperature stereoselective synthesis of α,β-unsaturated esters, fluorides, and nitriles from a wide array of aromatic, aliphatic, heterocyclic, and cyclic aldehydes and ketones, using a range of Wadsworth-Emmons (WE) phosphonates. Among the analogues of 1c [R = Me (1a), i-Pr (1b), Bn (1d)], 1a and 1b performed well, although longer reaction times were involved, and 1d led to poorer yields than 1c. Functionalities such as cyano, chloro, bromo, methoxy, amino, ester, and nitro were well tolerated. We were able to isolate and characterize (by X-ray means; see above) the reactive WE intermediate species formed from 2b and 1c.
