337365-72-7Relevant academic research and scientific papers
Cobalt(I)-catalyzed stereoselective olefination of alkylzinc reagents with aldehydes
Wang, Jin-Xian,Fu, Ying,Hu, Yulai,Wang, Kehu
, p. 1506 - 1510 (2003)
The efficient olefination from organozinc reagents with aldehydes is exploited in a new synthesis of aryl and alkyl olefins.
Catalyst-controlled reverse selectivity in C-C bond formation: NHC-Cu-catalyzed α-selective allylic alkylation with organolithium reagents
Pizzolato, Stefano F.,Giannerini, Massimo,Bos, Pieter H.,Fa?anás-Mastral, Martín,Feringa, Ben L.
supporting information, p. 8142 - 8145 (2015/05/20)
An efficient and highly α-selective copper-catalyzed allylic alkylation of allylic halides with organolithium reagents is presented. The use of N-heterocyclic carbenes as ligands is key to reverse the common γ-selectivity of this transformation and gives rise to the corresponding linear products with high levels of regioselectivity.
Cross-coupling reactions of alkenylsilanols with fluoroalkylsulfonates: Development and optimization of a mild and stereospecific coupling process
Denmark, Scott E.,Regens, Christopher S.
scheme or table, p. 2165 - 2168 (2011/05/05)
The development of an effective protocol for the palladium-catalyzed cross-coupling of (E)-alkenylsilanols with aryl triflates is described. A critical component in the optimization of this method was balancing the stability and reactivity of the triflates in the presence of a nucleophilic promoter. This report highlights the use of a slightly soluble Br?nsted base promoter that allows for a low, steady-state concentration of alkenyl(dimethyl)silanolate in solution, thus facilitating cross-coupling in preference to S-O bond cleavage of the triflate.
Stereospecific palladium-catalyzed cross-coupling of (E)- and (Z)-alkenylsilanolates with aryl chlorides
Denmark, Scott E.,Kallemeyn, Jeffrey M.
, p. 15958 - 15959 (2007/10/03)
The cross-coupling of geometrically defined (E)- and (Z)-alkenyl- and styrylsilanolates with a wide variety of aromatic and heteroaromatic chlorides has been achieved. Under catalysis by bulky, biphenyl-derived phosphines and allylpalladium chloride, the (preformed, stable) potassium salts of di-, tri- and tetrasubstituted alkenyldimethylsilanols undergo high yielding and highly stereospecific coupling to aryl chlorides in THF or dioxane. A variety of functional groups are compatible with these reaction conditions including nitro, ester, ketone, and nitrile. Both (E)- and (Z)-alkenylsilanolates coupled with nearly identical rate and efficiency. Copyright
Highly stereoselective hydrocarbation of terminal alkynes via Pt-Catalyzed Hydrosilylation/Pd-Catalyzed cross-coupling reactions
Denmark, Scott E.,Wang, Zhigang
, p. 1073 - 1076 (2007/10/03)
(matrix presented) The formal addition of an aryl-H or alkenyl-H bond across a terminal alkyne has been accomplished by the combination of platinum-catalyzed hydrosilylation followed by palladium-catalyzed cross-coupling. The use of the t-Bu3P-Pt(DVDS) catalyst in combination with tetramethyldisiloxane gave excellent regio- and stereoselectivity with a number of alkyne substrates. Subsequent, fluoride-promoted cross-coupling proceeded in high yield and stereospecificity for a variety of aryl halides.
OLEFINATION OF ALDEHYDES WITH TETRAALKYL-GEM-DIALUMOALKANES
Kuchin, A. V.,Markova, S. A.,Gorobets, E. V.,Tolstikov, G. A.
, p. 1034 - 1037 (2007/10/02)
A new method of cis-olefination, based on the reaction of aldehydes with geminal alumolithium reagents, is proposed.
