114262-84-9Relevant academic research and scientific papers
Synthesis of propargylic ethers by gold-mediated reaction of terminal alkynes with acetals
Furuta, Miyu,Sugiyama, Kyoko,Yamaguchi, Minami,Ueda, Hirofumi,Tokuyama, Hidetoshi
, p. 872 - 876 (2019)
A gold-catalyzed introduction of various terminal alkynes to acetals was investigated. Extensive optimization of the reaction conditions revealed that thermally stable cationic gold catalysts bearing bulky ligands such as 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene 3-1H-benzo[d][1,2,3]triazolyl gold trifluoromethanesulfonate (IPrAu(BTZ-H)OTf) were particularly suitable for the reaction. Additionally, significant solvent effects were observed. Ether solvents such as tetrahydrofuran (THF), cyclo pentyl methyl ether (CPME), and 1,4-dioxane were effective for the reaction. Studies on the scope of substrates and alkynes indicated that various alkynes and acetals were feasible to provide a wide range of propargylic ethers.
Palladium catalyzed cross-coupling and tandem cyclization-coupling of α-halo(thio)ethers with organotins
Bhatt,Shin, Dong-Soo,Falck,Mioskowski, Charles
, p. 4885 - 4888 (2007/10/02)
Pd(0) mediates the cross-coupling of organotins with a variety of α-haloethers/thioethers in moderate-good yields whereas an α-chloroacetoxyalkene failed to react. Tandem cyclization-coupling of the alkyl-palladium intermediate affords novel access to heterocycles.
Direct Formation of Reactive Alkynyltrichlorotins from 1-Alkynes, SnCl4, and Bu3N. A Mild Alkynylation Reagent of Aldehydes, Acetals, and Enones
Yamaguchi, Masahiko,Hayashi, Akio,Hirama, Masahiro
, p. 2479 - 2482 (2007/10/02)
A reagent system of 1-alkyne, SnCl4, and Bu3N alkynylates aldehydes, acetals,and enones under mild reaction conditions giving acetylenic alcohols, acetylenic ethers, and acetylenic ketones, respectively, in high yields.Alkynyltrichlorotins are shown to be
A Convenient Method for the Preparation of Secondary Propargylic Ethers. The Reaction of Acetals with 1-Trimethylsilyl-1-alkynes Promoted by the Combined Use of Catalytic Amounts of Tin(IV) Chloride and Zinc Chloride
Hayashi, Masaji,Inubushi, Atsuro,Mukaiyama, Teruaki
, p. 4037 - 4042 (2007/10/02)
In the coexistence of catalytic amounts of SnCl4 and ZnCl2, acetals undergo a coupling with 1-trimethylsilylalkynes to give secondary propargilic ethers in good yields.Similarly, propargilic ethers are directly produced from aldehydes by the treatment with alkoxytrimethylsilanes and 1-trimethylsilylalkynes under the same conditions.This catalyst system also efficiently promotes aldol reaction of silyl enol ethers with acetals or aldehydes, and the Michael reaction of silyl enol ethers with α,β-unsaturated ketones.
A Convenient Method for the Preparation of Secondary Propargylic Ethers. The Reaction of Acetals with 1-Trimethylsilylalkynes Promoted by the Combined Use of Catalytic Amounts of Tin(IV) Chloride and Zinc Chloride
Hayashi, Masaji,Inubushi, Atsuro,Mukaiyama, Teruaki
, p. 1975 - 1978 (2007/10/02)
In the coexistence of catalytic amounts of SnCl4 and ZnCl2, acetals undergo a coupling with 1-trimethylsilylalkynes in god yields to give secondary propargylic ethers, which are also directly produced from aldehydes by the reaction with alkoxytrimethylsil
