142389-19-3

Basic information

• Product Name: Borane, tris(3-phenylpropyl)-
• CAS NO: 142389-19-3
• Molecular Formula: C27H33B
• Molecular Weight: 368.37
• Mol File: 142389-19-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Borane, tris(3-phenylpropyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Borane, tris(3-phenylpropyl)-(142389-19-3)
• EPA Substance Registry System: Borane, tris(3-phenylpropyl)-(142389-19-3)

Safety Data

• Hazardous Substances Data: 142389-19-3(Hazardous Substances Data)

Upstream product

• 300-57-2 allylbenzene 
• 14044-65-6 borane-THF 
• 13292-87-0 dimethylsulfide borane complex 
• 13292-87-0 dimethyl sulfide borane 

Downstream Products

• 1448775-62-9 (R)-1-(4-chlorophenyl)-4-phenylbutan-1-ol 
• 126314-17-8 1-(4-chlorophenyl)-4-phenylbutan-1-ol 
• 1448775-63-0 (R)-1-cyclohex-1-enyl-4-phenylbutan-1-ol 
• 1448775-79-8 1-cyclohex-1-enyl-4-phenylbutan-1-ol 
• 16169-88-3 1-phenylprop-2-ynyl acetate 
• 142389-12-6 2-(3-Phenyl-propyl)-[1,4]naphthoquinone 
• 14010-87-8 1-(3-phenyl-propyl)-1,2,3,4-tetrahydro-benzo[b]borinine 

Relevant articles and documents

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.

A Concise and Atom-Economical Suzuki-Miyaura Coupling Reaction Using Unactivated Trialkyl- and Triarylboranes with Aryl Halides

A concise and atom-economical Suzuki-Miyaura coupling of trialkyl- and triarylboranes with aryl halides is described. This new protocol represents the first general, practical method that efficiently utilizes peralkyl and peraryl groups of the unactivated trialkyl- and triarylboranes for the Suzuki-Miyaura coupling reaction.

Enantioselective alkylation of aldehydes using functionalized alkylboron reagents catalyzed by a chiral titanium complex

A practical method is developed for the synthesis of enantioenriched functionalized secondary alcohols through catalytic enantioselective alkylation of aldehydes. Functionalized alkylboron reagents, [FG-(CH2) n]3B (FG = Br, TIPSO, PhtN, CO2iPr, and CN) prepared from terminal olefin precursors by hydroboration, undergo enantioselective addition to aldehydes in the presence of a catalytic amount (5 mol %) of 3-(3,5-diphenylphenyl)-H8-BINOL and excess titanium tetraisopropoxide to afford the corresponding functionalized alcohols in high enantioselectivities up to 99% ee.