828-15-9

Upstream product

• 109-72-8 n-butyllithium 
• 622-25-3 1-(2-chlorovinyl)benzene 
• 103-64-0 bromostyrene 
• 71-43-2 benzene 
• 16619-61-7 1-phenyl-2-phenylthioethene 
• 35843-79-9 (6-chloro-1-hexyn-1-yl)benzene 
• 16664-48-5 6-bromo-1-phenyl-1-hexyne 
• 693-25-4 n-pentylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 109-65-9 1-bromo-butane 
• 42599-24-6 E-styryl iodide 
• 543-63-5 n-butylmercuric chloride 
• 42930-39-2 n-butylzinc chloride 

Downstream Products

• 1536240-42-2 (1-phenylhexan-2-yl)phosphinic acid 
• 1743-30-2 2-Hydrazino-1-phenyl-hexan 

Relevant academic research and scientific papers

Selective hydroboration of equilibrating allylic azides

The iridium(i)-catalyzed hydroboration of equilibrating allylic azides is reported to provide only the anti-Markovnikov product of alk-1-ene isomers in good yields and with good functional group tolerance.

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.

Visible photocatalysis of novel oxime phosphonates: Synthesis of β-aminophosphonates

A novel type of oxime phosphonate was synthesized and used in the intermolecular cascade radical addition reaction of alkenes to access β-aminophosphonates via visible-light-driven N-centered iminyl radical-mediated and redox-neutral selective C-P single-bond cleavage in an active phosphorus radical route. The procedure is characterized by its ability to achieve the construction of Csp3-P and Csp3-N bonds without the requirement for oxidants and bases.

Photoinduced Nickel-Catalyzed Chemo- and Regioselective Hydroalkylation of Internal Alkynes with Ether and Amide α-Hetero C(sp3)-H Bonds

A direct hydroalkylation of disubstituted alkynes with unfunctionalized ethers and amides was achieved in an atom-efficient and additive-free manner through the synergistic combination of photoredox and nickel catalysis. The protocol was effective with a wide range of internal alkynes, providing products in a highly selective fashion. Notably, the observed regioselectivity is complementary to conventional radical addition processes. Mechanistic investigations suggest that the photoexcited iridium catalyst facilitated the nickel activation via single-electron transfer.

Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents

Palladium-catalyzed conjunctive cross-coupling is used for the synthesis of enantioenriched allylboron reagents. This reaction employs nonsymmetric bis(alkenyl)borates as substrates and appears to occur by a mechanism that involves selective activation of the less substituted alkene followed by migration of the more substituted alkene during the course of a Pd-induced metalate rearrangement.

Improvements and Applications of the Transition Metal-Free Asymmetric Allylic Alkylation using Grignard Reagents and Magnesium Alanates

Two new N-heterocyclic carbene (NHC) ligands have been synthesized and employed in the transition metal-free asymmetric allylic alkylation (AAA) mediated by Grignard reagents and magnesium alanates. The employment of these ligands showed high yields and improved regio- and enantioselectivity in the formation of tertiary and quaternary stereocenters. Moreover, the low catalyst loading (up to 0.3 mol%) and high scalability (up to 10 mmol) of this improved methodology provide a convenient access to biologically active compounds and synthetically valuable intermediates.

Direct catalytic cross-coupling of organolithium compounds

Catalytic carbon-carbon bond formation based on cross-coupling reactions plays a central role in the production of natural products, pharmaceuticals, agrochemicals and organic materials. Coupling reactions of a variety of organometallic reagents and organic halides have changed the face of modern synthetic chemistry. However, the high reactivity and poor selectivity of common organolithium reagents have largely prohibited their use as a viable partner in direct catalytic cross-coupling. Here we report that in the presence of a Pd-phosphine catalyst, a wide range of alkyl-, aryl- and heteroaryl-lithium reagents undergo selective cross-coupling with aryl- and alkenyl-bromides. The process proceeds quickly under mild conditions (room temperature) and avoids the notorious lithium halogen exchange and homocoupling. The preparation of key alkyl-, aryl- and heterobiaryl intermediates reported here highlights the potential of these cross-coupling reactions for medicinal chemistry and material science.

Dinuclear iron complex-catalyzed cross-coupling of primary alkyl fluorides with aryl grignard reagents

Iron-catalyzed cross-coupling of nonactivated primary alkyl fluorides with aryl Grignard reagents has been achieved by using the low-coordinate dinuclear iron complex [(IPr2Me2)Fe(μ2-NDipp) 2Fe(IPr2Me2)] as the catalyst. This iron-catalyzed C(sp3)-F bond arylation reaction is applicable to a variety of aryl Grignard reagents and primary alkyl fluorides. The product pattern suggests the involvement of a radical-type mechanism for its C-F bond scission step.

Synthesis, reactivity, and catalytic application of a nickel pincer hydride complex

The nickel(II) hydride complex [(MeN2N)Ni-H] (2) was synthesized by the reaction of [(MeN2N)Ni-OMe] (6) with Ph2SiH2 and was characterized by NMR and IR spectroscopy as well as X-ray crystallography. 2 was unstable in solution, and it decomposed via two reaction pathways. The first pathway was intramolecular N-H reductive elimination to give MeN2NH and nickel particles. The second pathway was intermolecular, with H2, nickel particles, and a five-coordinate Ni(II) complex [(MeN2N)2Ni] (8) as the products. 2 reacted with acetone and ethylene, forming [( MeN2N)Ni-OiPr] (9) and [(MeN 2N)Ni-Et] (10), respectively. 2 also reacted with alkyl halides, yielding nickel halide complexes and alkanes. The reduction of alkyl halides was rendered catalytically, using [(MeN2N)Ni-Cl] (1) as catalyst, NaOiPr or NaOMe as base, and Ph2SiH2 or Me(EtO)2SiH as the hydride source. The catalysis appears to operate via a radical mechanism.