73349-18-5

Upstream product

• 37490-22-5 2-[(E)-1-hexenyl]-1,3,2-benzodioxaborole 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 27975-79-7 1-phenyloct-1-yn-3-ol 
• 693-02-7 hex-1-yne 
• 1119-67-1 1-iodo-1-hexyne 
• 4440-01-1 lithium phenylacetylide 
• 693-04-9 butyl magnesium bromide 
• 18685-03-5 (E)-1-(4-chlorobut-3-en-1-ynyl)benzene 
• 218769-66-5 ((Z)-3-Methylselanyl-oct-3-en-1-ynyl)-benzene 
• 536-74-3 phenylacetylene 
• 173439-67-3 (E)-1-butyltelluro-1-hexene 
• 16644-98-7 (E)-1-iodohexene 
• 32584-71-7 diphenyl(phenylethynyl)stibine 
• 39556-65-5 2-butylethynyl methyl selenide 

Relevant academic research and scientific papers

Highly substituted enyne formation by coupling reaction of alkenylzirconium compounds with alkynyl halides

Alkenylzirconium compounds, which were prepared by carbozirconation or hydrozirconation of alkynes, reacted with alkynyl halides in the presence of CuCl to give highly substituted 1,3-enynes in good yields. This reaction was done conveniently in one-pot from alkynes.

Iron-catalyzed cross-coupling reactions of terminal alkynes with vinyl iodides

A convenient iron-catalyzed cross-coupling reaction of terminal alkynes with vinyl iodides is reported. The reaction was applicable to various acetylenes and vinyl iodides. The present reaction provides an efficient, environmentally friendly protocol to a

Palladium-catalyzed cross-coupling reaction of ethynylstibanes with organic halides

The reaction of ethynylstibanes (1a-g) with vinyl halides or triflate in the presence of a palladium catalyst led to the formation of cross-coupling products (5a-g, 10-12) in good to moderate yield, along with homo-coupling products (6a-g). A similar reaction of ethynyldiphenylstibane (1a) with aryl iodides (13a-i) also gave cross-coupling products (14a-i), although the yields were relatively low. The yields of the cross-coupling products were highly dependent on the nature of the solvent employed, and good results were obtained when the reaction was carried out in HMPA or amines such as diethylamine and morpholine. The results imply that HMPA and amine used as solvents facilitate transmetallation of the ethynyl group on 1 to the palladium by intermolecular coordination between antimony and oxygen (for HMPA) or nitrogen (for amine).

Stereoselective preparation of conjugated E-enynes from E-vinylic tellurides and terminal alkynes via Sonogashira cross-coupling

E-Vinylic tellurides undergo a direct cross-coupling reaction with terminal alkynes In the presence of palladium(II)/Cul In Et3N at room temperature to give E-enynes In good yields. The methodology represents a general and efficient protocol for carrying out the synthesis of E-enynes under mild conditions with complete retention of configuration.

First Example of Alkynyliodonium Tosylates coupling with 1,1-Bimetalloalkenes of Selenium and Zirconium

Hydrozirconation of internal acetylenic selenides afforded 1,1-bimetalloalkenes, (E)-α-selanylvinylzirconium, which can cross-couple with alkynyliodonium tosylates directly in the presence of Pd(PPh3)4 as the catalyst.

Stereoselective manganese-catalyzed coupling reaction of conjugated chloroenynes and chlorodienes with Grignard reagents

In the presence of the soluble complex MnCl2?2LiCl (3%), conjugated chloroenynes and chlorodienes readily react with alkyl Grignard reagents in THF-DMPU to afford stereoselectively enynes and dienes in good to excellent isolated yields.

A novel synthesis of (Z)-enynes and (Z)-enediynes from prop-2-ynyl alcohols

The conjugated (Z)-enynes and (Z)-enediynes were synthesized by dehydration of prop-2-ynyl alcohols with polyphosphoric acid trimethysilyl ester.

The Synthesis of Internal Conjugated (E)-Enynyldialkylboranes and Their Applications to the Syntheses of Conjugated Alkynones, Conjugated (E)-Enynes, and Conjugated Enynes Bearing an Unsaturated Group on the Double Bond

Internal conjugated (E)-enynyldialkylboranes were synthesized by successive reactions of 1-iodo-1-alkynes with dialkylboranes and 1-alkynyllithiums in 31-79percent yields. (E)-Enynyldialkylboranes, thus obtained, gave regio- and/or stereospecifically defined corresponding conjugated alkynones by alkaline hydrogen peroxide oxidation, conjugated (E)-enynes by protonolysis with acetic acid, and conjugated enynes bearing an unsaturated group on the internal alkenyl carbon atom by bis(acetylacetonato)copper-catalyzed cross-coupling reaction with allyl bromide or 1-bromo-1-hexyne respectively.

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

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.

Bis(acetylacetonato)copper Catalyzed Cross-coupling Reaction of Alkenyldicyclohexylborane with 1-Bromo-1-alkyne or 3-Bromo-1-propene

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.