93184-61-3Relevant articles and documents
Alkylation of Terminal Alkynes under Zinc Lewis Acid Catalysis and Its Mechanistic Studies
Osano, Mana,Kida, Takeru,Yonekura, Kyohei,Tsuchimoto, Teruhisa
supporting information, p. 2825 - 2831 (2019/04/13)
With a zinc Lewis acid catalyst and proton sponge in toluene, terminal alkynes were found to undergo the alkylation by alkyl triflates to provide unsymmetrical internal alkynes. This is the first example that a simple alkyl chain other than benzylic and norbornyl units can be introduced onto the alkynyl carbon atom under Lewis acid catalysis. Mechanistic studies revealed that the activation of the alkyne by the zinc Lewis acid and proton sponge is the trigger of the reaction to give a monoalkynylzinc species, which successively reacts with the alkyl triflate to afford the internal alkyne. A radical pathway is unlikely in this system. (Figure presented.).
Synthesis of five-membered unsaturated compounds from ketones via cyanophosphates under neutral conditions: [1,5]-C–H insertion of alkylidene carbenes generated by tetrazole fragmentation
Yoneyama, Hiroki,Uemura, Kenji,Usami, Yoshihide,Harusawa, Shinya
, p. 6109 - 6117 (2017/09/29)
Cyanophosphates (CPs) can easily be prepared via the reactions of carbonyl compounds with diethyl phosphorocyanidate (DEPC) in the presence of LiCN (cat.) under non-aqueous conditions. Treatment of ketone-derived CPs with TMSN3/Bu2Sn
STEREOSELECTIVE CYCLIC CARBOLITHIATION OF ALKYNE DERIVATIVES. A STEREOSELECTIVE SYNTHESIS OF EXOCYCLIC ALKENES
Wu, Guangzhong,Cederbaum, Fredrick E.,Negishi, Ei-ichi
, p. 493 - 496 (2007/10/02)
(Trimethylsilyl)alkyne derivatives that are lithiated in the δ position via non-radical routes can cyclize in a stereoselective manner (>96-98percent) to give exocyclic alkenes containing five-membered carbocycles in high yields.
