82954-89-0

Usage

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 3283, 1996 DOI: 10.1016/0040-4039(96)00576-X

Upstream product

• 98-86-2 acetophenone 
• 75927-49-0 pinacol vinylboronate 
• 97-93-8 triethylaluminum 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 74-84-0 ethane 
• 110-82-7 cyclohexane 
• 73183-34-3 bis(pinacol)diborane 
• 74-85-1 ethene 

Downstream Products

• 1352127-75-3 4,4,5,5-tetramethyl-2-(1-phenylpentan-3-yl)-1,3,2-dioxaborolane 
• 959685-46-2 (S)-4,4,5,5-tetramethyl-2-(1-phenylpentan-3-yl)-1,3,2-dioxaborolane 
• 1136153-61-1 N-((1S,2S)-2-hydroxy-1-phenylbut-1-yl)-2-methylpropane-2-sulfonamide 
• 1136153-71-3 N-((2S)-2-hydroxy-2-phenylbut-1-yl)-2-methylpropane-2-sulfonamide 
• 1257661-30-5 2-(2-(4-chlorophenyl)butan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1240815-92-2 (R)-4,4,5,5-tetramethyl-2-(2-phenylbutan-2-yl)-1,3,2-dioxaborolane 
• 1201898-74-9 (S)-4,4,5,5-tetramethyl-2-(2-phenylbutan-2-yl)-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Copper-Catalyzed Tandem Hydrocupration and Diastereo- and Enantioselective Borylalkyl Addition to Aldehydes

We report the copper-catalyzed stereoselective addition of in situ generated chiral boron-α-alkyl intermediates to various aldehydes including α,β-unsaturated aldehydes under mild conditions. This tandem and multicomponent method facilitated the synthesis of enantiomerically enriched 1,2-hydroxyboronates bearing contiguous stereocenters in good yield with high diastereo- and enantioselectivity up to a ratio greater than 98:2. In particular, α,β-unsaturated aldehydes were successfully used as electrophiles in Cu?H catalysis through 1,2-addition without significant reduction. The resulting 1,2-hydroxyboronates were used in various transformations.

Aluminum Hydride Catalyzed Hydroboration of Alkynes

An aluminum-catalyzed hydroboration of alkynes using either the commercially available aluminum hydride DIBAL-H or bench-stable Et3Al?DABCO as the catalyst and H-Bpin as both the boron reagent and stoichiometric hydride source has been developed. Mechanistic studies revealed a unique mode of reactivity in which the reaction is proposed to proceed through hydroalumination and σ-bond metathesis between the resultant alkenyl aluminum species and HBpin, which acts to drive turnover of the catalytic cycle.

Catalyst-controlled selectivity in the C-H borylation of methane and ethane

The C-H bonds of methane are generally more kinetically inert than those of other hydrocarbons, reaction solvents, and methane functionalization products.Thus, developing strategies to achieve selective functionalization of CH4 remains a major

σ-borane and dihydroborate complexes of ruthenium

Room temperature reaction of the bis(dihydrogen) complex RuH2(H2)2(PCy3)2 (1) with excess pinacol borane (HBpin) generates the novel complex RuH[(μ-H)2Bpin](σ-HBpin)(PCy3)2 (2) by loss of dihydrogen. Complex 2 was characterized spectroscopically and by X-ray crystallography. It contains two pinacolborane moieties coordinated in a different fashion, one as a dihydroborate (B-H distances : 1.58(3) and 1.47(3) A) and the other as a σ-borane (B-H distance: 1.35(3) A). In addition, reaction of 1 with one equiv of HBpin yields total conversion to a new complex tentatively formulated as RuH[(μ-H)2Bpin](H2)(PCy3)2 (3) on the basis of NMR data. In the presence of excess HBpin, 3 is converted to 2. Furthermore, under an atmosphere of dihydrogen, a C7D8 solution of 2 rapidly converts to 3 and finally regenerates 1 over a much longer period. Thus, complex 3 is an intermediate in the formation of 2 from 1. In these processes the borane is eliminated as HBpin later hydrolyzed to BpinOBpin. Selective hydroboration of ethylene (3 bar) into C2H5Bpin is achieved using 1 or 2 as catalyst precursors in toluene, whereas in THF, competitive formation of the vinylborane C2H3Bpin (56% under 20 bar of C2H4) can be favored. Copyright