93184-61-3Relevant academic research and scientific papers
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.).
Sonogashira reactions of alkyl halides catalyzed by NHC [CNN] pincer nickel(II) complexes
Wang, Zijing,Zheng, Tingting,Sun, Hongjian,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter
, p. 11465 - 11470 (2018/07/24)
C(carbene)N(amido)N(amine)-pincer nickel(ii) complexes [iPrCNN-Ni-Br] (6), [nBuCNN-Ni-Br] (7) and [BnCNN-Ni-Cl] (8) were synthesized. The catalytic performance of complexes 6-8 for Sonogashira cross-coupling reactions was
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.
Preparation of (Z)-Alkenes, Ketones, and Alkynes via Trialkyltin Chloride Induced Intramolecular Transfer Reaction of Lithium 1-Alkynyltrialkylborates. Stereoselective Synthesis of the Sex Pheromones of the Douglas Fir Tussock Moth, the Gipsy Moth, and the Wild Silkmoth Antheraea poly...
Wang, Kung K.,Chu, Kai-Hsuan
, p. 5175 - 5178 (2007/10/02)
Trialkyltin chloride was used to induce selective migration of a primary alkyl group from the boron atom to the adjacent acetylenic carbon atom of lithium 1-alkynyltrialkylborate complexes derived from B-alkyl-9-borabicyclononanes and 1-lithio-1-alkynes.Protonolysis of the resultant olefinic intermediate substituted with boron and tin functionalities on the adjacent vinyl carbon atoms provided the corresponding (Z)-alkene.Oxidation or iodination afforded the corresponding ketone or alkyne, respectively.The high selectivity of 9-borabicyclononane as ahydroborating agent toward the terminal double bond allowed easy incorporation of internal double bond and triple bond into the alkyl group of the starting B-alkyl-9-borabicyclononane.Various types of diene, enyne, enone, ynone and diyne were synthesized.These reactions were also successfully adopted for the stereoselective synthesis of sex pheromones of the Douglas fir tussock moth, the gypsy moth, and the wild silkmoth Antheraea polyphemus.
