55976-13-1Relevant academic research and scientific papers
Novel type of carbozirconation reaction of alkynes
Suzuki, Noriyuki,Kondakov, Denis Y.,Kageyama, Motohiro,Kotora, Martin,Hara, Ryuichiro,Takahashi, Tamotsu
, p. 4519 - 4540 (1995)
Novel type of carbozirconation reaction of alkynes is reported. Treatment of zirconocenealkyne complexes, zirconacyclopentenes, or zirconacyclopentadienes with allylic compounds gave allylzirconation products of alkynes. Carbozirconation of alkynes with zirconacyclopentenes or zirconacyclopentadienes involved β,β'-C-C bond cleavage reaction of zirconacycles. Reactions of zirconacyclopentenes with homoallyl bromides afforded allylcyclopropane derivatives as carbozirconation products.
Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis
Patel, Niki R.,Kelly, Christopher B.,Jouffroy, Matthieu,Molander, Gary A.
supporting information, p. 764 - 767 (2016/03/01)
Single-electron transmetalation via photoredox/nickel dual catalysis provides the opportunity for the construction of Csp3-Csp2 bonds through the transfer of alkyl radicals under very mild reaction conditions. A general procedure for the cross-coupling of primary and secondary (bis-catecholato)alkylsilicates with alkenyl halides is presented. The developed method allows not only alkenyl bromides and iodides but also previously underexplored alkenyl chlorides to be employed. (Chemical Equation Presented).
Cross-coupling reaction of allylic and benzylic carbonates with organo[2-(hydroxymethyl)phenyl]dimethylsilanes
Nakao, Yoshiaki,Ebata, Shiro,Chen, Jinshui,Imanaka, Hidekazu,Hiyama, Tamejiro
, p. 606 - 607 (2008/02/07)
The title reaction is found to proceed in the presence of a palladium catalyst and in the absence of any activator. Various functional groups are tolerated to give a diverse range of 1,4-diene and diarylmethane products, which are ubiquitous units of natural products and pharmaceuticals. Copyright
Reduction of acetylenic compounds to (E)-olefins by alkali metals - An investigation of the scope
Brandsma, Lambert,Nieuwenhuizen, Willem F.,Zwikker, Jan W.,Maeeorg, Uno
, p. 775 - 779 (2007/10/03)
Efficient procedures have been developed for the stereospecific reduction by alkali metals of disubstituted acetylenes with long carbon chains. Acetylenes containing two or more (isolated) triple bonds are reduced considerably more easily than are monoyne
Efficient Conditions for the Palladium(II) Mediated Coupling of Organostannanes: The Synthesis of 1,3-Dienes, 1,4-Dienes, 1,3-Diynes and Biphenyls
Alcaraz, Lilian,Taylor, Richard J. K.
, p. 791 - 792 (2007/10/03)
Convenient conditions are described for the preparation of 1,3-dienes by vinylstannane homocoupling using palladium(II)-catalysis with oxygen (or air) for Pd(0)/Pd(II) reoxidation; related homo-couplings, and cross-coupling reactions with allylstannane, are used to obtain 1,3-diynes, biaryls and 1,4-dienes.
Silicon-Mediated Skipped Diene Synthesis. Application to the Melon Fly Pheromone
Wilson, Stephen R.,Zucker, Paul A.
, p. 4682 - 4693 (2007/10/02)
The 1,4-diene unit is a key structural feature of many fatty acid derived natural products including arachidonic acid, several of the leukotrienes, and a variety of insect pheromones.In this paper substituted cyclopropyl>carbinols are demonstrated to cleave redily, upon treatment with acid or upon conversion to the corresponding mesylates, to give mono- and disubstituted 1,4-pentadienes.Stereoselective formation of cis and trans olefins from diastereomeric carbinols has been examined.Control of configuration at the olefin derived from the trimethylsilyl-bearing terminus of the cyclopropane system was found to be only moderate while the olefin derived from the carbinol terminus of the cyclopropane system was produced with high trans stereoselectivity.From these results it is concluded that the cleavage of the cyclopropane ring is neither significantly accelerated by, nor strongly coupled to, cleavage of the carbon-silicon bond.The high stereoselectivity observed for the formation of the trans configuration at the olefin derived from the carbinol terminus has been applied to the synthesis of a constituent of the melon fly pheromone.
Novel and Convenient Method for the Stereo- and Regiospecific Synthesis of Conjugated Alkadienes and Alkenynes via the Palladium-Catalyzed Cross-Coupling Reaction of 1-Alkenylboranes with Bromoalkenes and Bromoalkynes
Miyaura, Norio,Yamada, Kinji,Suginome, Hiroshi,Suzuki, Akira
, p. 972 - 980 (2007/10/02)
Details of a new and general method for the stereo- and regiospecific synthesis of conjugated alkadienes and alkenynes are described.The reaction of (E)- or (Z)-1-alkenyldisiamylboranes, or 2-((E)-1-alkenyl)-1,3,2-benzodioxaboroles readily obtainable by hydroboration, with either (E)- or (Z)-1-alkenyl bromides in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium and bases such as sodium alkoxides gives the corresponding (E,E)-, (E,Z)-, (Z,E)-,or (Z,Z)-conjugated alkadienes stereo- and regiospecifically, while retaining the configurations of both the strating alkenylboranes and bromoalkenes.The reaction of (E)- and (Z)-1-alkenyldisiamylboranes with 1-bromoalkynes similarly provides a stereo- and regiospecific synthesis of conjugated (E)- and (Z)-alkenynes.A mechanism of this cross-coupling reaction, which involves the transmetalation between a 1-alkenylborane and an alkoxypalladium(II) complex generated through the metathetical displacement of a halogen atom from R(Pd(II)X with sodium alkoxide, is proposed.
NOVEL SYNTHESIS OF INTERNAL ALKENYLDIALKYLBORANE BY THE REACTION OF 1-HALO-1-ALKENYLDIALKYLBORANE WITH GRIGNARD REAGENT.
Arase,Hoshi,Masuda
, p. 209 - 213 (2007/10/02)
To synthesize internal alkenyldialkylboranes, coupling reactions were carried out by using 1-halo-1-alkenyldialkylboranes and Grignard reagents. Hydrogen peroxide oxidation and protonolysis with acetic acid of the reaction product revealed that internal (E)-alkenyldialkylborane was formed in 60-90% yield.
Bis(acetylacetonato)copper Catalyzed Cross-coupling Reaction of Alkenyldicyclohexylborane with 1-Bromo-1-alkyne or 3-Bromo-1-propene
Hoshi, Masayuki,Masuda, Yuzuru,Arase, Akira
, p. 2855 - 2856 (2007/10/02)
Bis(acetylacetonato)copper is capable of catalyzing cross-coupling reaction of alkenyldicyclohexylborane with 1-bromo-1-alkyne or 3-bromo-1-propene to give conjugated (E)-enzyme or (E)-1,4-diene in a highly stereoselective manner, respectively.
THE PALLADIUM-CATALYSED CROSS-COUPLING REACTION OF 1-ALKENYLBORANES WITH ALLYLIC OR BENZYLIC BROMIDES. CONVENIENT SYNTHESIS OF 1,4-ALKADIENES AND ALLYLBENZENES FROM ALKYNES VIA HYDROBORATION
Miyaura, Norio,Yano, Takashi,Suzuki, Akira
, p. 2865 - 2868 (2007/10/02)
The reaction of allylic or benzylic bromides with 1-alkenyldisiamylboranes readily available from 1-alkynes in the presence of sodium hydroxyde and catalytic amounts of tetrakis-(triphenylphosphine)palladium to give corresponding 1,4-alkadienes or allylbe
