177573-86-3

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 153724-93-7 2-[(E)-3-chloroprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 129423-29-6 [(1E)-3-phenylprop-1-en-1-yl]boronic acid 
• 10147-11-2 propargyl benzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 300-57-2 allylbenzene 
• 75927-49-0 pinacol vinylboronate 
• 97-94-9 triethyl borane 
• 1313878-07-7 (E)-1-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl acetate 
• 2043-61-0 cyclohexanecarbaldehyde 
• 55718-76-8 2-chloro-1,3,2-benzodioxaborole 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 84363-90-6 (1S,2R)-(-)-1,2-diphenylbut-3-en-1-ol 
• 1572039-97-4 3-[(S)-1-benzyl-2-(6-chloropyrimidin-4-yl)ethyl]benzoic acid ethyl ester 
• 1572040-10-8 methyl 3-[(2S)-1-(6-methoxypyrimidin-4-yl)-3-phenylpropan-2-yl]benzoate 
• 1572039-87-2 4-chloro-6-[(S)-2-(4-methylphenyl)-3-phenylpropyl]pyrimidine 
• 1572039-96-3 4-chloro-6-[(S)-2-(4-methoxyphenyl)-3-phenylpropyl]pyrimidine 
• 1572039-82-7 4-chloro-6-[(E)-3-phenylprop-1-en-1-yl]pyrimidine 
• 147609-46-9 2-(2E)-(3-phenyl-2-propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 147609-47-0 (Z)-PhCHCHCH₂BO₂(CMe₂)2 
• 84363-90-6 (1RS,2SR)-1,2-diphenyl-3-buten-1-ol 

Relevant academic research and scientific papers

Cs4B4O3F10: First Fluorooxoborate with [BF4] Involving Heteroanionic Units and Extremely Low Melting Point

Herein, a new congruently melting mixed-anion compound Cs4B4O3F10 has been characterized as the first fluorooxoborate with [BF4] involving heteroanionic units. Compound Cs4B4O3F10 possesses two highly fluorinated anionic clusters and therefore its formula can be expressed as Cs3(B3O3F6) ? Cs(BF4). The influence of [BF4] units on micro-symmetry and structural evolution was discussed based on the parent compound. More importantly, Cs4B4O3F10 shows the lowest melting point among all the available borates and thus sets a new record for such system. This work is of great significance to enrich and tailor the structure of borates using perfluorinated [BF4] units.

Transborylation of alkenylboranes with diboranes

Exchange of boryl moieties between alkenylboranes and diboron reagents has been postulated as a stereospecific cross-metathesis pathway with concomitant formation of mixed diboron reagents. DFT calculations propose a mechanism for the stereocontrolled C(sp2)-B/B′-B′ cross-metathesis with both symmetric and non-symmetric diboron reagents. This journal is

Electrochemical Hydroboration of Alkynes

Herein we reported the electrochemical hydroboration of alkynes by using B2Pin2 as the boron source. This unprecedented reaction manifold was applied to a broad range of alkynes, giving the hydroboration products in good to excellent yields without the need of a metal catalyst or a hydride source. This transformation relied on the possible electrochemical oxidation of an in situ formed borate. This anodic oxidation performed in an undivided cell allowed the formation of a putative boryl radical, which reacted on the alkyne.

Catalyst-free and solvent-free hydroboration of alkynes

The hydroboration of alkynes with pinacolborane (HBpin) under catalyst- and solvent-free conditions was demonstrated. Various alkynes were smoothly converted into alkenyl boronate esters in good to excellent yields at 110 °C. The gram-scale hydroboration

Solvent- and metal-free hydroboration of alkynes under microwave irradiation

Boronic esters are versatile building blocks extensively used in organic chemistry and essential to a variety of coupling reactions. In this work, the hydroboration reactions of alkynes were performed without metal catalysts using concomitant microwave ir

Silver-Catalyzed anti-Markovnikov Hydroboration of C-C Multiple Bonds

A simple silver salt (AgOAc)-catalyzed anti-Markovnikov-selective hydroboration of alkenes, 1,3-dienes, and alkynes with pinacolborane (HBpin) has been described. This strategy provides an efficient and practical method to access various alkyl-, allyl-, a

Lithium diisobutyl-: Tert-butoxyaluminum hydride (LDBBA) catalyzed hydroboration of alkynes and imines with pinacolborane

Lithium diisobutyl-tert-butoxyaluminum hydride (LDBBA)-catalyzed hydroboration of alkynes with pinacolborane (HBpin) was demonstrated. The hydroboration proceeded more efficiently with LDBBA than with other aluminum hydrides and afforded alkenyl boronates in moderate to good yields. In addition, high-yielding LDBBA-catalyzed hydroboration of imines was achieved. The coordination of anionic aluminate with lithium enables effective hydride transfer for hydroboration.

Stereoselective Synthesis of Trisubstituted Vinylboronates from Ketone Enolates Triggered by 1,3-Metalate Rearrangement of Lithium Enolates

An unprecedented stereoselective synthesis of trisubstituted vinylboronates is reported to proceed by direct borylation of lithium ketone enolates under transition-metal-free conditions. The stereospecific C?O borylation of lithium enolates was triggered by a carbonyl-induced 1,3-metalate rearrangement via a C-bound boron enolate. DFT calculations and control experiments revealed that the stereoselectivity is controlled by sterics. A variety of stereospecific trisubstituted vinylboronates, together with several tetrasubstituted vinylboronates, were conveniently synthesized with the newly developed methodology. Based on the transformation of stereospecific vinylboronate, a single isomer of Dienestrol was efficiently obtained.

Migratory Arylboration of Unactivated Alkenes Enabled by Nickel Catalysis

An unprecedented arylboration of unactivated terminal alkenes, featuring 1,n-regioselectivity, has been achieved by nickel catalysis. The nitrogen-based ligand plays an essential role in the success of this three-component reaction. This transformation displays good regioselectivity and excellent functional-group tolerance. In addition, the incorporation of a boron group into the products provides substantial opportunities for further transformations. Also demonstrated is that the products can be readily transformed into pharmaceutically relevant molecules. Unexpectedly, preliminary mechanistic studies indicate that although the metal migration favors the α-position of boron, selective and decisive bond formation is favored at the benzylic position.

Borane-Catalysed Hydroboration of Alkynes and Alkenes

Simple, commercially available borane adducts, H 3 B·THF and H 3 B·SMe 2, have been used to catalyse the hydroboration of alkynes and alkenes with pinacolborane to give the alkenyl and alkyl boronic esters, respectively. A