862776-52-1Relevant articles and documents
Vanadium(V)-mediated rearrangement/halogenation cascade: Synthesis of α-haloenones from propargyl alcohols
Zhao, Meng,Mohr, Justin T.
, p. 4115 - 4124 (2017/06/29)
A method is described for the oxidative Meyer–Schuster-type rearrangement of propargylic alcohols to (Z)-α-chloro- and α-iodoenones using VOCl3 as a multifunctional reagent. The vanadium reagent is found to serve as rearrangement promoter as well as an active chlorenium ion donor. Yields are improved when VOCl3 is employed in conjunction with N-halosuccinimide reagents, giving some insights into the complex mechanism.
Silver-catalyzed efficient synthesis of vinylene carbonate derivatives from carbon dioxide
Ugajin, Rie,Kikuchi, Satoshi,Yamada, Tohru
supporting information, p. 1178 - 1180 (2014/05/20)
It was found that the silver salt and base was an efficient catalytic system for the reaction of the secondary propargylic alcohol with carbon dioxide to afford various corresponding vinylene carbonate derivatives in good to high yields under mild conditions. Georg Thieme Verlag Stuttgart New York.
Highly diastereoselective synthesis of cyclopentenones via a one-pot gold catalysis, Nazarov cyclization and alkylation cascade
Liu, Meng-Qi,Zhou, Ai-Hua,Jiang, Shuang,Wang, Jia-Qi,Ye, Long-Wu
supporting information, p. 2161 - 2167 (2014/08/18)
Starting from readily available propargylic carboxylates, three sequential transformations [gold-catalyzed tandem reaction, scandium(III) trifluoromethanesulfonate catalyzed Nazarov cyclization, alkylation reaction] in a one-pot process led to the formation of cyclopentenone derivatives in excellent diastereoselectivities and moderate to good overall yields. Georg Thieme Verlag Stuttgart. New York.
Gold- and silver-catalyzed reactions of propargylic alcohols in the presence of protic additives
Pennell, Matthew N.,Turner, Peter G.,Sheppard, Tom D.
supporting information; experimental part, p. 4748 - 4758 (2012/05/04)
A wide range of primary, secondary and tertiary propargylic alcohols undergo a Meyer-Schuster rearrangement to give enones at room temperature in the presence of a gold(I) catalyst and small quantities of MeOH or 4-methoxyphenylboronic acid. The syntheses of the enone natural products isoegomaketone and daphenone were achieved using this reaction as the key step. The rearrangement of primary propargylic alcohols can readily be combined in a one-pot procedure with the addition of a nucleophile to the resulting terminal enone, to give β-aryl, β-alkoxy, β-amino or β-sulfido ketones. Propargylic alcohols bearing an adjacent electron-rich aryl group can also undergo silver-catalyzed substitution of the alcohol with oxygen, nitrogen and carbon nucleophiles. This latter reaction was initially observed with a batch of gold catalyst that was probably contaminated with small quantities of silver salt.
Tetrabutylammonium fluoride (TBAF)-catalyzed addition of substituted trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones
Chintareddy, Venkat Reddy,Wadhwa, Kuldeep,Verkade, John G.
supporting information; experimental part, p. 4482 - 4488 (2011/07/30)
Herein we report that tetrabutylammonium fluoride (TBAF) is a very efficient catalyst for the addition of trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones in THF solvent at room temperature. The reaction conditions are mild and oper
New application of n-halosuccinimide/PPh3 for the halogenation of propargyl alcohols to haloallenes
Du, Xin,Dai, Yao,He, Ren,Lu, Shirong,Bao, Ming
experimental part, p. 3940 - 3949 (2010/03/25)
An efficient and convenient new method has been developed for the preparation of haloallenes from propargyl alcohols by a reagent combination of N-halosuccinimide and triphenylphosphine. Chloroallenes 2 and bromoallenes 3 were obtained exclusively in mode
Lewis base-catalyzed additions of alkynes using trialkoxysilylalkynes
Lettan II, Robert B.,Scheidt, Karl A.
, p. 3227 - 3230 (2007/10/03)
(Chemical Equation Presented) The Lewis base-catalyzed additions of alkynyl nucleophiles to aldehydes, ketones, and imines is described. Mechanistic studies strongly indicate that the use of new triethoxysilylalkynes facilitates access of a reactive hyper
