1883-35-8

Upstream product

• 100-42-5 styrene 
• 14044-65-6 borane-THF 
• 13292-87-0 dimethylsulfide borane complex 
• 110-51-0 borane pyridine 

Downstream Products

• 64-04-0 phenethylamine 
• 16169-88-3 1-phenylprop-2-ynyl acetate 
• 98493-50-6 C₁₆H₁₇B 
• 13213-09-7 1-(2-phenyl-ethyl)-1-bora-indane 
• 1393591-19-9 C₂₅H₂₄ 
• 5450-75-9 4-methyl-N-(2-phenylethyl)benzenesulfonamide 
• 5722-91-8 1,2-diphenyl-2-(phenylamino)ethanone 
• 82537-54-0 N-(2-Oxo-1,2-diphenyl-ethyl)-3,N-diphenyl-propionamide 

Relevant academic research and scientific papers

Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of Anti-δ,δ-Disubstituted Homoallylic Alcohols

The trialkylborane/O2-mediated reaction of propargyl acetates having a tributylstannyl group at an alkyne terminus with aldehydes in a THF-H2O solvent system gave anti-δ,δ-disubstituted homoallylic alcohols with good to high diastereoselectivity. Intriguingly, two alkyl groups derived from trialkylborane were embedded into the reaction product. The trialkylborane plays a key role not only as a radical initiator but also as a source of alkyl radicals.

BORON-CONTAINING ORGANIC COMPOUND

PROBLEM TO BE SOLVED: To provide a boron-containing organic compound exhibiting an excellent mobility by a condensation heterocyclic structure having not less than 2 nitrogen atoms at a center part of the skeleton and obtained by condensing not less than 3 rings, and further cross-linking with boron. SOLUTION: According to the present invention, a boron-containing organic compound is provided, the compound represented by the following chemical formula (1) where a ring X1 and X2 in formula (1) may be same or different, and express an aromatic ring, a heteroaromatic ring or these condensation rings which may be substituted, Y1 expresses a condensation heterocyclic ring containing not less than 2 nitrogen atoms, and obtained by condensing not less than 3 rings, and R1-R6 may be same or different, and express hydrogen, halogen, or a univalent substituent. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Palladium-Catalyzed Three-Component Reaction of 3-(Tri-n- butylstannyl)allyl Acetates, Aldehydes, and Triorganoboranes: An Alternative to the Carbonyl Allylation Using α,γ-Substituted Allylic Tin Reagents

A three-component reaction of 3-(tri-n-butylstannyl)allyl acetates, aldehydes, and triorganoboranes in the presence of a palladium-Xantphos catalyst system predominately gave (E)-anti-homoallylic alcohols with high diastereoselectivity and good to high levels of alkene stereocontrol. An efficient chirality transfer was observed when an enantioenriched substrate was employed. The reaction was initiated by the formation of an allylic gem-palladium/stannyl intermediate, which subsequently underwent allylation of the aldehyde by an allyltributyltin followed by a coupling reaction of the in-situ-generated (E)-vinylpalladium acetate with the triorganoborane.

Facile synthesis of (Z)-anti-homoallylic alcohols from 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes via a palladium-catalyzed three-component reaction

A palladium-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes was developed. The present protocol provides facile access to synthetically useful (Z)-anti-homoallylic alcohols with high diastereoselect

Pd-catalyzed three-component reaction of 3-(Pinacolatoboryl)ally acetates, aldehydes, and organoboranes: A new entry to stereoselective synthesis of (Z)- anti -homoallylic alcohols

The Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl acetates, aldehydes, and organoboranes is described. The reaction is initiated by the formation of an allylic gem-palladium/boryl intermediate, which then undergoes allylation of aldehydes by allylboronates followed by a coupling reaction of in situ generated (Z)-vinylpalladium acetates with organoboranes to provide the (Z)-anti-homoallylic alcohols with high levels of diastereoselectivity and alkene stereocontrol.

Scope and post-transformations for the borane-isocyanide multicomponent reactions: Concise access to structurally diverse heterocyclic compounds

A recently described family of multicomponent reactions (MCRs) involving isocyanides, aldehydes, dipolarophiles and alkylboranes that yield highly substituted aziridines, oxazolidines and pyrrolidines has been studied in detail. In this work the scope of these processes is significantly increased by preparing the borane input through hydroboration of alkenes or organometallic processes, in tandem with the MCR. The aldehyde range is also expanded, and indole-3-carbaldehydes yield reactive imines and bis-indolyloxazolidines, depending on the electron density of the heterocycle. Finally, the obtained adducts constitute an ideal platform to generate structurally diverse compounds using simple post-condensation modifications. In this way, indole imines undergo stereoselective hydrocyanation and oxazolidines are reductively opened to give amino alcohols. Additionally, palladium-, ruthenium- and gold-catalyzed processes lead to a variety of complex heterocycles. The methodology is simple, efficient and highly divergent, leading to an array of interesting scaffolds for medicinal chemistry. Copyright

Generation of organolithium compounds bearing super silyl ester and their application to Matteson rearrangement

It's super-silyl-fragilithyl-ester-aryl-docious: The super silyl group is a strong protecting group for carboxylic acids and provides a method for direct lithiation that is compatible with the ester moiety. Organolithium compounds bearing a super silyl ester react with a variety of electrophiles in high yields (see scheme). The reaction of lithiated super silyl chloroacetate with a boron compound gives α-functionalization of the ester moiety by Matteson rearrangement. Copyright

Domino Friedel-crafts-type cyclizations of difluoroalkenes promoted by the α-cation-stabilizing effect of fluorine: An efficient method for synthesizing angular PAHs

In order to synthesize polycyclic aromatic hydrocarbons with nonlinear arrangements (angular PAHs), acid-promoted domino cyclizations of 1,1-difluoroalk-1-enes and 1,1-difluoroalka-1,3-dienes were studied. 1,1-Difluoroalkenes, each bearing two aryl substituents, were regioselectively protonated with FSO3H·SbF5 to generate fluorine-stabilized carbocations, which readily underwent domino Friedel-Crafts-type cyclizations to give carbocycles based on 6/n/m/6 ring systems (n,m=5-7) in good to high yields. Protonation of 1,1-difluoroalka-1,3- dienes took place at their electron-rich methylene (CH2) carbon atoms in the presence of milder acids such as camphorsulfonic acid and trifluoromethanesulfonic acid. Domino cyclizations of the resulting fluorine-stabilized allylic carbocations afford carbocycles based on 6/6/6/6 or 6/6/5/6 ring systems in high yields.

Friedel-Crafts-type cyclization of 2,2-difluorovinyl ketones via α-fluorocarbocations and its application in domino cyclizations

2,2-Difluorovinyl ketones bearing an aryl group undergo Friedel-Crafts-type cyclization via carbocations stabilized by α-fluorines on treatment with a trimethylsilylating agent [Me3SiOTf or Me3SlB(OTf) 4]. The reaction aff

Friedel-crafts cyclization of 1,1-difluoroalk-1-enes: Synthesis of benzene-fused cyclic ketones via α-fluorocarbocations

1,1-Difluoroalk-1-enes bearing a phenyl group at the C-3, -4, or -5 position, readily obtained from 2,2,2-trifluoroethyl p-toluenesulfonate, are treated with FSO3H·SbF5 to undergo Friedel-Crafts cyclization in (CF3)2CHOH. The cyclization takes place via α-fluorocarbocations, followed by spontaneous hydrolysis of the C-F bond to afford bicyclic ketones including a five, six, or seven-membered ring in good yield.