99464-24-1

Upstream product

• 143-15-7 1-dodecylbromide 
• 69322-49-2 trans-1-(9-borabicyclo{3.3.1}non-9-yl)-2-phenylethene 
• 100-42-5 styrene 
• 112-52-7 1-chlorododecane 
• 536-74-3 phenylacetylene 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 75618-27-8 lauryl triflate 
• 26537-05-3 C₁₅H₃₀O 
• 100-58-3 phenylmagnesium bromide 
• 1120-36-1 1-tetradecene 
• 66003-76-7 Diphenyliodonium triflate 
• 4292-19-7 1-Iodododecane 
• 99464-15-0 1-Methyl-4-((E)-1-phenyl-tetradec-1-ene-3-sulfonyl)-benzene 

Relevant academic research and scientific papers

Multicatalytic Stereoselective Synthesis of Highly Substituted Alkenes by Sequential Isomerization/Cross-Coupling Reactions

Starting from readily available alkenyl methyl ethers, the stereoselective preparation of highly substituted alkenes by two complementary multicatalytic sequential isomerization/cross-coupling sequences is described. Both elementary steps of these sequences are challenging processes when considered independently. A cationic iridium catalyst was identified for the stereoselective isomerization of allyl methyl ethers and was found to be compatible with a nickel catalyst for the subsequent cross-coupling of the in situ generated methyl vinyl ethers with various Grignard reagents. The method is compatible with sensitive functional groups and a multitude of olefinic substitution patterns to deliver products with high control of the newly generated C=C bond. A highly enantioselective variant of this [Ir/Ni] sequence has been established using a chiral iridium precatalyst. A complementary [Pd/Ni] catalytic sequence has been optimized for alkenyl methyl ethers with a remote C=C bond. The final alkenes were isolated with a lower level of stereocontrol. Upon proper choice of the Grignard reagent, we demonstrated that C(sp2) - C(sp2) and C(sp2) - C(sp3) bonds can be constructed with both systems delivering products that would be difficult to access by conventional methods.

Mild Base Promoted Nucleophilic Substitution of Unactivated sp3-Carbon Electrophiles with Alkenylboronic Acids

Diverse alkenylboronic acids react smoothly with various sp3-carbon electrophiles such as unactivated alkyl triflates in the presence of mild bases such as K3PO4. The reaction protocol is very mild and thereby enables high functional group tolerance. This transition metal-free condition is orthogonal towards the classic transition metal catalyzed Suzuki coupling. (Figure presented.).

Palladium-catalyzed intermolecular Heck reaction of alkyl halides

Intermolecular Heck reaction of common alkyl halides, a longstanding problem in palladium catalysis, is realized with a simple Pd/dppf catalyst. Both primary and secondary alkyl halides are suitable for coupling with aromatic olefins. Single electron transfer from (dppf)Pd0 to alkyl halide initiated the catalytic cycle and gave alkyl radicals. This journal is the Partner Organisations 2014.

Microwave-assisted palladium-catalyzed arylation of styrenes and alkenes with diaryliodonium salts

Highly effective microwave-assisted palladium-catalyzed arylation of styrenes and alkenes with diaryliodonium salts have been developed, giving styrenes in high yields without ligand in 60 s.

Cobalt-catalyzed trimethylsilylmethylmagnesium-promoted radical alkenylation of alkyl halides: A complement to the Heck reaction

A cobalt complex, [CoCl2(dpph)] (DPPH = [1,6- bis(diphenylphosphino)hexane]), catalyzes an intermolecular styrylation reaction of alkyl halides in the presence of Me3SiCH2MgCl in ether to yield β-alkylstyrenes. A variety of alkyl halides including alkyl chlorides can participate in the styrylation. A radical mechanism is strongly suggested for the styrylation reaction. The sequential isomerization/styrylation reactions of cyclopropylmethyl bromide and 6-bromo-1-hexene provide evidence of the radical mechanism. Crystallographic and spectroscopic investigations on cobalt complexes reveal that the reaction would begin with single electron transfer from an electron-rich (diphosphine)bis(trimethylsilylmethyl)cobalt(II) complex followed by reductive elimination to yield 1,2-bis(trimethylsilyl)ethane and a (diphosphine)cobalt(I) complex. The combination of [CoCl 2(dppb)] (DPPB = [1,4-bis(diphenylphosphino)butane]) catalyst and Me3SiCH2-MgCl induces intramolecular Heck-type cyclization reactions of 6-halo-1-hexenes via a radical process. On the other hand, the intramolecular cyclization of the prenyl ether of 2-iodophenol would proceed in a fashion similar to the conventional palladium-catalyzed transformation. The nonradical oxidative addition of carbon(sp2)-halogen bonds to cobalt is separately verified by a cobalt-catalyzed cross-coupling reaction of alkenyl halides with Me3SiCH2MgCl with retention of configuration of the starting vinyl halides. The cobalt-catalyzed intermolecular radical styrylation reaction of alkyl halides is applied to stereoselective variants. Styrylations of 1-alkoxy-2-bromocyclopentane derivatives provide trans-1-alkoxy-2-styrylcyclopentane skeletons, one of which is optically pure.

Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols

A simple new protocol for the high yielding Suzuki-Miyaura cross-couplings of aryl chlorides with aryl boronic acids using a palladium/imidazolium salt catalytic system is presented. The first examples of a palladium/imidazolium salt protocol for sp3-sp3 Suzuki-Miyaura couplings of alkyl halides are also disclosed.

Cobalt-catalyzed heck-type reaction of alkyl halides with styrenes

(Chemical Equqtion Presentation) A cobalt complex, CoCl2[1,6-bis(diphenylphosphino)hexane], catalyzes an alkylation reaction of styrenes in the presence of Me3SiCH2MgCl in ether to yield β-alkylstyrenes. A variety of alkyl halides including alkyl chlorides can be employed as an alkyl source. A radical mechanism is strongly suggested for this alkylation reaction. Copyright

PALLADIUM-CATALYZED REGIO- AND STEREOSELECTIVE DESULFONYLATION OF ALLYLIC SULFONES WITH LiHBEt3. APPLICATION TO THE SYNTHESIS OF SQUALENE

Allylic p-tolyl sulfones were easily desulfonylated to the corresponding alkenes by LiHBEt3 in the presence of a catalytic amount of under mild conditions with the preservation of the original stereochemistry.This reaction was successfully applied to the synthesis of squalene.