42353-94-6

Upstream product

• 591-50-4 iodobenzene 
• 1942-45-6 4-Octyne 
• 4406-77-3 2-Phenyl-1,3,2-dioxaborinane 
• 960-71-4 triphenylborane 
• 18291-94-6 phenyl(ethyl)silanediol 
• 98-80-6 phenylboronic acid 
• 143-66-8 sodium tetraphenyl borate 
• 853955-69-8 [2-(hydroxymethyl)phenyl]dimethyl(phenyl)silane 
• 38111-44-3 phenylzinc(II) bromide 
• 100-58-3 phenylmagnesium bromide 
• 925-90-6 ethylmagnesium bromide 
• 108-86-1 bromobenzene 
• 591-51-5 phenyllithium 
• 100-59-4 phenylmagnesium chloride 

Relevant academic research and scientific papers

Trisubstituted alkenes from alkynes and aryl iodides by boron-to-zinc transmetallation and palladium(0) catalyzed cross coupling

Alkenylethylzincs, obtained from the corresponding trialkenylboranes by transmetallation with diethylzine, couple with aryl iodides in the presence of Pd(PPh3)4, 0.19-0.28 molpercent, to produce trisubstituted alkenes in good isolated yields.Both the transmetallation and subsequent coupling occur with complete retention of stereochemistry.

Nickel-catalysed hydroarylation of alkynes using arylboron compounds: Selective synthesis of multisubstituted arylalkenes and aryldienes

Bis(1,5-cyclooctadiene)nickel was found to be an effective catalyst for the addition of the aryl group of arylboron compounds to alkynes in the presence of a proton source, which gives various multisubstituted alkenylarenes or dienylarenes selectively.

Rh-catalyzed addition of boronic acids to alkynes for the synthesis of trisubstituted alkenes in a biphasic system - Mechanistic study and recycling of the Rh/m-TPPTC catalyst

The versatile preparation of trisubstituted alkenes via selective Rh-catalyzed arylation of alkynes is described in water and in a water/toluene biphasic system. For hydrophobic alkyl alkynes, the reaction afforded either alkenes or dienes depending on the temperature and the solvent conditions. Aryl, heteroaryl, silylated and alkyl substituted alkynes reacted equally well with various boronic acids, leading regioselectively to functionalized alkenyl derivatives in high yields (65-99%). The mechanism was investigated in toluene/water mixture or water and involves a vinylrhodium complex. The efficient recycling of the Rh/m-TPPTC system is disclosed with excellent yield (92-96%) and purity of the alkene.

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.

P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation

Asymmetric copper-catalyzed allylic alkylation between allyl bromides and alkyl Grignard reagents using a P-chiral monophosphorus ligand is described. A range of terminal olefins bearing tertiary or quaternary carbon centers were formed in good branched/linear selectivities and excellent enantioselectivities at copper loadings as low as 0.5 mol %.

Geometry-Constrained Iminopyridyl Palladium-Catalyzed Hydroarylation of Alkynes to Prepare Tri-substituted Alkenes Using Alcohol as Reductant

We developed an efficient and straightforward method to prepare tri-substituted alkenes through palladium-catalyzed hydroarylation of alkynes with aryl bromides. Diarylacetylenes and alkyl(aryl)acetylenes could be well hydroarylated with various aryl bromides in moderate to excellent yields. Mechanistic studies suggested that alcohol was the reductant to provide hydride through β-H elimination. Gram scale reaction further demonstrated the practicality and efficiency of the newly developed strategy. (Figure presented.).

Hydrophenylation of internal alkynes with boronic acids catalysed by a Ni-Zn hydroxy double salt-intercalated anionic rhodium(III) complex

[Rh(OH)6]3- intercalated Ni-Zn mixed basic salt (Rh/NiZn) acts as an efficient catalyst for the hydrophenylation of internal alkynes with arylboronic acids under mild conditions. The turnover number per Rh site approached 740 in the reaction between 4-octyne and phenylboronic acid. The catalytic monomeric Rh(iii) complex is stabilised within the NiZn interlayers, attributable to a strong electrostatic interaction, promoting its re-use.

Cobalt-catalyzed addition of arylzinc reagents to alkynes to form ortho-alkenylarylzinc species through 1,4-cobalt migration

Migratory carbometalation: A cobalt-Xantphos complex catalyzes the addition of an arylzinc reagent to an unactivated internal alkyne; the reaction most likely involves insertion of the alkyne into an arylcobalt species and vinyl-to-aryl 1,4-cobalt migration, followed by transmetalation with the arylzinc reagent. Interception of the resulting ortho-alkenylarylzinc species with electrophiles allows access to 1-alkenyl arenes functionalized in the 2-position. Copyright

Iron-catalyzed aryl- and alkenyllithiation of alkynes and its application to benzosilole synthesis

Phenyl- and vinyllithiums having an alkyl substituent at their ortho- and cis-position, respectively, readily added to alkynes in the presence of 5 mol% of Fe(acac)3. The reaction of o-(trimethylsilyl)phenyllithium with alkynes gave benzosilole

Manganese-catalyzed cross-coupling reaction between aryl grignard reagents and alkenyl halides

(Chemical Equation Presented) Aryl Grignard reagents react stereospecifically with alkenyl halides in the presence of manganese chloride (10%) to afford good yields of cross-coupling products.