66619-22-5

Upstream product

• 1942-46-7 5-decyne 
• 71-43-2 benzene 
• 108-86-1 bromobenzene 
• 38111-44-3 phenylzinc(II) bromide 
• 143-66-8 sodium tetraphenyl borate 
• 661488-99-9 Dibutyl-((E)-1-butyl-2-phenylsulfanyl-hex-1-enyl)-borane 
• 693-02-7 hex-1-yne 
• 137298-83-0 (E)-5-(phenylthio)dec-5-ene 
• 591-51-5 phenyllithium 
• 105763-12-0 (E)-2-(1-butyl-1-hexenyl)-1,3,2-dioxaborinane 
• 106865-24-1 (Z)-5-Iodo-5-decene 
• 104293-08-5 (5E)-5-iodo-dec-5-ene 
• 591-50-4 iodobenzene 
• 127410-78-0 (E)-5-(diethoxymethylsilyl)-5-decene 

Relevant academic research and scientific papers

Recyclable and reusable PdCl2(PPh3)2/PEG-400/H2O system for the hydrophenylation of alkynes with sodium tetraphenylborate

A stable and efficient PdCl2(PPh3)2/PEG-400/H2O catalytic system for the hydrophenylation reaction of alkynes has been developed. In the presence of 3 mol% PdCl2(PPh3)2 and 2 equiv. of HOAc, the hydrophenylation of both terminal and internal alkynes with sodium tetraphenylborate proceeded smoothly in a mixture of PEG-400 and water at room temperature or 50 °C to afford a variety of phenyl-substituted alkenes in moderate to high yields. The isolation of the products was easily performed by extraction with petroleum ether, and the PdCl2(PPh3)2/PEG-400/H2O system could be readily recycled and reused six times without apparent loss of catalytic activity.

Palladium-Catalyzed C?H Alkenylation of Arenes with Alkynes: Stereoselective Synthesis of Vinyl Chlorides via a 1,4-Chlorine Migration

A directing group-free, ligand-promoted palladium-catalyzed C?H arylation of internal alkynes with simple arenes was developed. Alkenyl chlorides resulting from a 1,4-chlorine migration or trisubstituted alkenes were produced in moderate to good yields depending on the type of alkyne.

Cobalt-catalysed synthesis of highly substituted styrene derivatives via arylzincation of alkynes

A new two-step procedure was developed by carbozincation of internal and terminal alkynes to synthesise highly functionalised vinylzinc bromides. Various tri and tetrasubstituted alkenes were prepared in moderate to good yields under mild reaction conditions in a stereo-selective manner. This methodology represents an interesting alternative to previously known methods. This journal is

Palladium-catalyzed hydrophenylation of alkynes with sodium tetraphenylborate under mild conditions

(Chemical Equation Presented) In an aqueous solution of acetic acid, PdCl2(PPh3)2 showed high catalytic activity for the hydrophenylation of both terminal and internal alkynes with sodium tetraphenylborate (NaBPh4) under mild conditions, affording phenyl alkenes in moderate to excellent yields.

Stereoselective cis-addition of aromatic C - H bonds to alkynes catalyzed by dinuclear palladium complexes

Reactions of alkynes with arenes proceeded in the presence of dinuclear palladium complexes and trialkylboranes to yield alkyne hydroarylation products with high stereoselectivity. In the reactions of monosubstituted benzenes, meta and para products were

Chalcogen electrophile induced rearrangement of 1-alkynyltrialkyl borates: Controlled syntheses of trisubstituted olefins from 1-alkynes

The reaction of 1-alkynyltrialkyl borates with sulfenyl, selenenyl and tellurenyl halides produces β-chalcogeno alkenylboranes in good yields, with a cis relationship between the boron and the chalcogen moities. Protodeborylation of these compounds by acetic acid, or by a transmetalation-protonolysis sequence, leads to vinyl chalcogenides, which can be converted to alkenes by means of a nickel catalyzed coupling with Grignard reagents. Since the last two steps occur with retention of the stereochemistry, the overall sequence represents a highly regio- and stereoselective olefin synthesis.

TRANSITION METAL ?-COMPLEXES IN ORGANIC SYNTHESIS 5. CROSS-COUPLING OF ORGANOMANGANESE COMPOUNDS WITH ALKENYL IODIDES

Aryl organomanganese compounds ArMnX and Ph3MnLi (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4, p-BrC6H4, α-naphthyl; X = Cl, Br) react with alkenyl iodides RR1C=CR2I (R = H, Pr, Bu, i-Bu, C6H13, CH2=CHCH2, Ph; R1 = H, Pr, C5H11; R2 = H, Pr, SiMe3) in THF at 0-20 deg C to give cross-coupling products RR1C=CR2Ar in high yields.

Palladium-catalyzed cross-coupling reaction of alkenylalkoxysilanes with aryl and alkenyl halides in the presence of a fluoride ion

Alkenyl-monoalkoxydimethylsilanes, dialkoxymethylsilanes, and trialkoxysilanes undergo palladium catalyzed cross-coupling reaction with alkenyl and aryl halides in the presence of tetra-n-butylammonium fluoride. A one-pot transformation of a homopropargyl

Vinylic Organoboranes. 11. A Highly Stereospecific and Regiospecific Synthesis of Trisubstituted Alkenes via Organoboranes

A highly stereospecific synthesis of trisubstituted alkenes using (E)- and (Z)-2-(1-substituted-1-alkenyl)-1,3,2-dioxaborinanes is presented. (E)-2-(1-Substituted-1-alkenyl)-1,3,2-dioxaborinanes (1), as described previously, readily react with organolithium or Grignard reagents in diethyl ether at -78 deg C to form the corresponding "ate" complexes.Treatment of these "ate" complexes with iodine in methanol induces the migration of the alkyl group from boron to the adjacent carbon, followed by a base-induced deiodoboronation to afford stereodefined trisubstituted alkenes in good yields (50-82percent) and in excellent stereochemical purities (97percent).Similarly (Z)-2-(1-substituted-1-alkenyl)-1,3,2-dioxaborinanes (2), easily obtainable by a previous procedure, react with organolithium or Grignard reagents, followed by treatment with iodine and base, to produce the stereoisomeric trisubstituted alkenes in good yields (65-82percent) and in excellent isomeric purites (97percent).These two procedures provide a convenient route to any of the six possible trisubstituted alkenes, R1CH=CR2R3.