7642-12-8

Upstream product

• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 104-87-0 4-methyl-benzaldehyde 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 74-85-1 ethene 
• 4160-52-5 1-(4-methylphenyl)butan-1-one 
• 101671-00-5 (E)-2-(4-methylphenyl)-1-nitroethene 
• 97-93-8 triethylaluminum 
• 96-10-6 diethylaluminium chloride 
• 563-46-2 2-Methyl-1-butene 
• 20574-99-6 1-(but-3-en-1-yl)-4-methylbenzene 
• 104-81-4 4-Methylbenzyl bromide 
• 617-86-7 triethylsilane 
• 3160-38-1 (E)-4-p-tolylbut-3-en-2-one 
• 2386-64-3 ethylmagnesium chloride 

Downstream Products

• 866996-62-5 1-(1,2-dichloro-butyl)-4-methyl-benzene 
• 141298-85-3 1-(2-Chloro-1-methylsulfanyl-butyl)-4-methyl-benzene 
• 1335126-74-3 (R)-((R)-1-phenyl-2,2,2-trichloroethyl) (E)-4-(4-methylphenyl)but-3-en-2-ylcarbamate 

Relevant academic research and scientific papers

A facile preparation of geometrically pure alkenyl, alkynyl, and aryl conjugated Z-alkenes: Stereospecific synthesis of bombykol

Ni- and Pd-catalyzed cross coupling reactions of 2-alkenyl, 2-alkynyl, and 2-aryl substituted (1Z)-1-bromoalkene with alkyl Grignard reagents gave 1-alkyl substituted (1Z,3E)-diene, (1Z)-en-3-yne, and (1Z)-2-arylethene, each in good yield. When (trimethylsilyl)-methylmagnesium chloride was used as the Grignard reagent, conjugated Z-allylsilane was produced. Bombykol, (10E, 12Z)-10,12-hexadecadien-1-ol, a sex pheromone of female moss, Bombyx mori, was synthesized stereospecifically. 2000 Elsevier Science Ltd.

Method for synthesizing 1, 2-disubstituted olefin through reaction of terminal group olefin and sulfoxide

The invention discloses a method for synthesizing 1, 2-disubstituted olefin by reaction of terminal olefin and sulfoxide. According to the method, terminal olefin with sulfoxide make reaction in one pot in the presence of ferric salt and hydrogen peroxide to generate the 1, 2-disubstituted olefin. sulfoxide is simultaneously used as a hydrocarbylation reagent and a solvent of olefin, and a reaction product is 1, 2-disubstituted olefin of which a terminal carbon atom in terminal olefin is coupled with a sulfoxide alkyl group, so that an olefin carbon chain is increased; the reaction conditionsare mild, the selectivity is high, the yield is high, and industrial production is facilitated.

Method for synthesizing alkyl olefin through coupling of double-bond carbon-hydrogen bond and saturated carbon-hydrogen bond

The invention discloses a method for synthesizing alkyl olefin through coupling of a double-bond carbon-hydrogen bond and a saturated carbon-hydrogen bond. According to to the method, one-pot reactionis implemented on olefin and sulfoxide in the presence of ferric salt and hydrogen peroxide to generate alkyl olefin; in the method, sulfoxide is simultaneously used as a hydrocarbylation reagent anda solvent of olefin, and a reaction product is alkyl olefin from sulfoxide alkyl coupled with olefin carbon atoms, so that an olefin carbon chain is increased; the reaction conditions are mild, the selectivity is good, the yield is high, and industrial production is facilitated.

METHODS OF BORYLATION AND USES THEREOF

The present invention relates, in general terms, to methods of borylation and uses thereof. In particular, the present invention provides a method of borylating an alkene compound by contacting the compound with a boron compound, a Fe pre-catalyst and a protic additive. The borylation occurs at a vicinal (β) position to an electron donating or electron withdrawing moiety of the compound.

Iron-Catalyzed Tunable and Site-Selective Olefin Transposition

The catalytic isomerization of C-C double bonds is an indispensable chemical transformation used to deliver higher-value analogues and has important utility in the chemical industry. Notwithstanding the advances reported in this field, there is compelling demand for a general catalytic solution that enables precise control of the C═C bond migration position, in both cyclic and acyclic systems, to furnish disubstituted and trisubstituted alkenes. Here, we show that catalytic amounts of an appropriate earth-abundant iron-based complex, a base and a boryl compound, promote efficient and controllable alkene transposition. Mechanistic investigations reveal that these processes likely involve in situ formation of an iron-hydride species which promotes olefin isomerization through sequential olefin insertion/β-hydride elimination. Through this strategy, regiodivergent access to different products from one substrate can be facilitated, isomeric olefin mixtures commonly found in petroleum-derived feedstock can be transformed to a single alkene product, and unsaturated moieties embedded within linear and heterocyclic biologically active entities can be obtained.

Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins

The dealkenylative alkenylation of alkene C(sp3)?C(sp2) bonds has been an unexplored area for C?C bond formation. Herein 64 examples of β-alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β-nitrostyrenes by ozone/FeII-mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso-moracin and the drug (E)-metanicotine.

Enzymatic Primary Amination of Benzylic and Allylic C(sp3)-H Bonds

Aliphatic primary amines are prevalent in natural products, pharmaceuticals, and functional materials. While a plethora of processes are reported for their synthesis, methods that directly install a free amine group into C(sp3)-H bonds remain unprecedented. Here, we report a set of new-to-nature enzymes that catalyze the direct primary amination of C(sp3)-H bonds with excellent chemo-, regio-, and enantioselectivity, using a readily available hydroxylamine derivative as the nitrogen source. Directed evolution of genetically encoded cytochrome P411 enzymes (P450s whose Cys axial ligand to the heme iron has been replaced with Ser) generated variants that selectively functionalize benzylic and allylic C-H bonds, affording a broad scope of enantioenriched primary amines. This biocatalytic process is efficient and selective (up to 3930 TTN and 96percent ee), and can be performed on preparative scale.

Controllable Isomerization of Alkenes by Dual Visible-Light-Cobalt Catalysis

We report herein that thermodynamic and kinetic isomerization of alkenes can be accomplished by the combination of visible light with Co catalysis. Utilizing Xantphos as the ligand, the most stable isomers are obtained, while isomerizing terminal alkenes over one position can be selectively controlled by using DPEphos as the ligand. The presence of the donor–acceptor dye 4CzIPN accelerates the reaction further. Transformation of exocyclic alkenes into the corresponding endocyclic products could be efficiently realized by using 4CzIPN and Co(acac)2 in the absence of any additional ligands. Spectroscopic and spectroelectrochemical investigations indicate CoI being involved in the generation of a Co hydride, which subsequently adds to alkenes initiating the isomerization.

A mild method for indium(III)-catalyzed 1,4-hydrosilylation of α,β-enone esters with triethylsilane and trifluoroacetic acid

A chemo- and stereoselective 1,4-hydrosilylation of α,β-enone esters was developed using triethylsilane and trifluoroacetic acid under indium chloride catalysis. Georg Thieme Verlag Stuttgart ? New York.

Iron-catalysed, hydride-mediated reductive cross-coupling of vinyl halides and Grignard reagents

An iron-catalysed, hydride-mediated reductive cross-coupling reaction has been developed for the preparation of alkanes. Using a bench-stable iron(ii) pre-catalyst, reductive cross-coupling of vinyl iodides, bromides and chlorides with aryl- and alkyl Grignard reagents successfully gave the products of formal sp3-sp3 cross-coupling reactions.