167693-19-8

Usage

Type of compound

Boronic acid derivative

Structure

Cyclic compound containing a boron atom and a cyclopentylidene group

Organic synthesis

Formation of carbon-carbon and carbon-heteroatom bonds

Pharmaceutical industry

Building block for the synthesis of various drug compounds

Materials science

Building block in the production of organic electronic materials and polymers

Upstream product

• 1528-30-9 methylenecyclopentane 
• 73183-34-3 bis(pinacol)diborane 
• 72824-04-5 4,4,5,5-tetramethyl-2-(1-propenyl)-1,3,2-dioxaborolane 
• 120-92-3 cyclopentanone 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 60484-91-5 (cyclopentylidenemethoxy)trimethylsilane 
• 872-53-7 cyclopentanealdehyde 
• 2468-56-6 1-iodo-5-hexyne 
• 66977-99-9 6-bromo-1-hexyne 

Relevant academic research and scientific papers

Alkenyl boron compound and preparation method and application thereof

The invention discloses an alkenyl boron compound and a preparation method and application thereof. The preparation method comprises the following steps: in a protective atmosphere, enabling a uniformly mixed reaction system containing a lithium enol reag

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.

The Boron-Wittig Olefination of Aldehydes and Ketones with Bis[(pinacolato)boryl]methane: an Extended Reaction Scope

Preparation of 2,2-disubstituted and 2-monosubstituted alkenylboronic acid esters from aliphatic and aromatic ketones and aldehydes by the boron-Wittig olefination with bis[(pinacolato)boryl]methane was examined and applied on the multigram scale. The influence of the substrate steric and electronic features on the overall efficiency and stereochemical outcome of the reaction was studied. Additionally, a series of diversely functionalized (hetera)cycloalkylidenemethyl and (hetera)cycloalkyl boronic acid-derived building blocks was synthesized.

Carboboration of Alkynes with Cyclodextrin-Encapsulated N-Heterocyclic Carbene Copper Complexes

The copper-catalyzed carboboration of various alkynes was investigated with a modified N-heterocyclic carbene-capped α-cyclodextrin copper(I) complex in which the reactive copper center is deeply encapsulated in the cyclodextrin (CD) cavity. The methylborylation of terminal alkynes was found to give linear (L) (E)-vinyl boron isomers as the major isomers, as expected from the previously proposed “perpendicular” approach of the alkyne to the Cu–B bond, and methylation of the vinyl boron copper intermediate. Under similar conditions, the intramolecular carboboration reaction with terminal alkynes functionalized by alkyl halides, led to exocyclic vinyl boronate species as the major isomer. However, an endocyclic (Z)-isomer was also observed in some cases. This isomer was not previously observed and is unexpected considering the “classical” mechanism. The direct generation of boron functionalized (Z)-alkenes by carboboration of alkynes is unprecedented.

Copper(I)-catalyzed regio- and stereoselective intramolecular alkylboration of propargyl ethers and amines

The copper(I)-catalyzed regio- and stereoselective intramolecular alkylation of propargyl ethers and amines bearing an alkyl electrophilic moiety has been developed. The reaction showed high functional group tolerance and gave highly functionalized alkenylboronates bearing heterocyclic rings, which are versatile synthetic intermediates in organic chemistry. The borylation products can be transformed into multisubstituted alkenes through stereospecific transformations. Mechanistic studies showed that the chemo- and stereoselectivity of copper(I)-catalyzed borylation depends on the type of leaving group. Density functional theory calculations suggested that the regioselectivity of the borylcupration of the alkyne is controlled by the electronic effect of the oxygen atom of the propargyl ether in combination with the steric congestion between the boryl group and the substituent at the propargylic position.

DIHYDROPYRIMIDIN-2-ONE COMPOUNDS AND MEDICAL USE THEREOF

A compound of Formula [I] or a pharmaceutically acceptable salt thereof: wherein each symbol is defined as in the specification.

Rhodium catalysed dehydrogenative borylation of alkenes: Vinylboronates via C-H activation

We present herein a high yield, highly selective catalytic synthesis of vinylboronate esters (VBEs), including 1,1-disubstituted VBEs, from alkenes without significant hydrogenation or hydroboration, using the simple catalyst precursor, trans-[RhCl(CO)(PPh3)2] (1), and the diboron reagents B2pin2 (2a, pin = pinacolato = OCMe 2CMe2O) or B2neop2 (2b, neop = neopentylglycolato = OCH2CMe2CH2O), or the monoboron reagent HBpin, all of which are commercially available. The reactions were conducted at 80 °C using conventional heating, or in a microwave reactor at 150 °C. The Royal Society of Chemistry.

Synthesis of functionalized vinyl boronates via ruthenium-catalyzed olefin cross-metathesis and subsequent conversion to vinyl halides

Functionalized vinyl pinacol boronates suitable for Suzuki cross-coupling reactions are synthesized using ruthenium-catalyzed olefin cross-metathesis of 1-propenyl pinacol boronate and various alkenes, including functionalized and 1,1-disubstituted alkenes. The resultant boronate cross products are stereoselectively transformed into predominantly Z-vinyl bromides and E-vinyl iodides. The vinyl bromides may be synthesized in a two-step, one-pot synthesis from a variety of olefins, resulting in a Z-selective formal vinyl bromide cross-metathesis reaction.

Rhodium catalysed dehydrogenative borylation of vinylarenes and 1,1-disubstituted alkenes without sacrificial hydrogenation - A route to 1,1-disubstituted vinylboronates

The complex trans-[Rh(Cl)(CO)(PPh3)2] (1) is an efficient catalyst precursor for the dehydrogenative borylation of alkenes without consumption of half the alkene substrate by hydrogenation, giving useful vinylboronate esters including 1,1-disubstituted derviatives that cannot be made by alkyne hydroboration.