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Upstream product

• 591-50-4 iodobenzene 
• 37730-25-9 (E)-1-Lithio-1-octen 
• 629-05-0 n-octyne 
• 4440-01-1 lithium phenylacetylide 
• 344453-19-6 n-decylzinc iodide 
• 52356-93-1 (Z)-1-octenyl iodide 
• 104089-17-0 ethyl 4-(iodozincio)butanoate 
• 98-80-6 phenylboronic acid 
• 42599-17-7 (E)-1-iodo-1-octene 
• 927-77-5 n-propylmagnesium bromide 
• 56798-08-4 (E)-1-bromo-2-iodoethylene 
• 591-51-5 phenyllithium 

Relevant academic research and scientific papers

Stereoretentive Pd-catalyzed kumada-corriu couplings of alkenyl halides at room temperature

Stereoselective palladium-catalyzed Kumada-Corriu reactions of functionalized alkenyl halides and a variety of Grignard reagents, including those bearing β-hydrogen atoms and sensitive functional groups, can be carried out at room temperature using a new combination of reagents.

Ligand effects on the stereochemical outcome of suzuki-miyaura couplings

The ligands associated with various Pd catalysts play a crucial role in determining the stereochemistry of cross-couplings between boronic acids and Z-alkenyl halides. A ligand on palladium has been found that leads to the desired products under mild conditions and in high yields that, in most cases, retain their Z-olefin geometry.

Ligand effects on Negishi couplings of alkenyl halides

Negishi couplings at olefinic centers do not always occur with the anticipated maintenance of stereochemistry. The source of erosion has been traced to the ligand, and a modified method has been developed that solves the stereochemical issue and significantly improves yields of Negishi couplings in general.

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.

Use of InCl3 as a cocatalyst and a Cl2Pd(DPEphos)- P(2-Furyl)3 catalyst system for one-pot hydrometalation-cross- coupling and carbometalation-cross-coupling tandem processes

One-pot conversion of alkynes to regio- and stereodefined alkenylmetals containing Al and Zr via hydrometalation or carbometalation followed by their Pd-catalyzed cross-coupling with (E)-ICH=CHBr or (E)-ICH=CHCl proceeds cleanly and selectively to give the corresponding 1-halo1,3-dienes in excellent yields using a catalyst system consisting of Cl2Pd(DPEphos), DIBAL-H, and TFP (catalyst A) with InCl3 as a cocatalyst.

Oxovanadium(V)-induced oxidation of alkenylzirconocenes for facile inter- and intramolecular coupling

The oxidation reaction of (E)-1-alkenylchlorozirconocenes with an oxovanadium(V) compound at room temperature led to intermolecular homocoupling, giving the corresponding (E,E)-dienes stereoselectively. (E)-1-Alkenyl-1-alkynylzirconocenes underwent the oxovanadium(V)-induced intramolecular cross-coupling of organic substituents on zirconium, leading to the stereoselective formation of the (E)-enynes.

Palladium-catalyzed or -promoted reductive carbon-carbon coupling. Effects of phosphines and carbon ligands

The reaction of Cl2Pd(PEt3)2 with 2 equiv of (E)-t-BuCH=CHLi, t-BuCCLi, or MeLi gives the corresponding R12Pd(PEt3)2 in a nearly quantitative yield without producing R1R1, where R1=(E)-t-BuCH=CH, t-BuCC, or Me.The reaction of PhLi or PhZnCl gives Ph2Pd(PEt3)2 and biphenyl in approximately 90 and 10percent yields, respectively.On the other hand, the corresponding reaction of Cl2Pd(PPh3)2 produces R1R1 in >95percent yield within 1 h in each case.Attempts to detect R12Pd(PPh3)2 have failed.Their formation as unstable intermediates may be inferred from those cases where PEt3, PPhMe2, and PPh2Me are used.The ease of formation of R1R1 is inversely proportional to the basicity of PR3, i.e., PEt3 12Pd(PEt3)2 and R1R2Pd(PEt3)2 prepared in this study are trans.All but one are stable for 3 h at 22 deg C. trans-PhPd(PEt3)2, however, undergoes a slow reductive elimination to give (E)-n-HexCH=CHPh in 70percent within 12 h at room temperature.Biphenyl and 2 can be produced in high yields based on Pd via the corresponding R12Pd(PR3)2, where PR3 is PEt3, PPhMe2, or PPh2Me, through the use of 8 equiv. of R1Li.Similar acceleration effects have also been observed in the reaction of R1R2Pd(PR3)2 with an excess of R1Li, R2I, or PR3.However, the reductive elimination reactions of (p-Tol)PhPd(PEt3)2 promoted by p-TolLi and PhI give significant amounts of homo-coupled products.These results can be explained in terms of various associative mechanisms that have previously been proposed.The reaction of aryl- or alkenyl-zinc chlorides with aryl or alkenyl iodides catalyzed by "Pd(PR3)2" can give the desired cross-coupled products in >/= 60percent yields.However, only "Pd(PPh3)2" leads to uniformly high cross/homo ratios.With PEt3, PPh2Me, and PhMe2, cross-homo scrambling occurs to considerable extents, although the reaction of t-BuCCZnCl with PhI catalyzed by "Pd(PEt3)2" is exceptional.The high cross/homo ratio observed with PPh3 is consistent with some dissociative mechanisms but does not appear to be consistent with any associative mechanisms.

A SIMPLE SYNTHESIS OF TRANS, TRANS-1,3-DIENES FROM TERMINAL ALKYNES USING CoCl2/Ph3P/NaBH4

The cobalt hydride reagent prepared in situ in THF at -20 deg C using CoCl2/NaBH4/Ph3P in the 1:1:4 ratio hydrodimerizes terminal alkynes into the corresponding trans, trans-1,3-dienes in good yields (65 to 86percent).