74213-49-3

Upstream product

• 1192-37-6 methylenecyclohexane 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 53282-55-6 (trimethylsiloxymethylidene)cyclohexane 
• 73183-34-3 bis(pinacol)diborane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 134361-02-7 Lithium; cyclohexylidene-methanolate 
• 74213-42-6 trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)silane 
• 13311-54-1 2,3-dimethyl-2,3-butanediol monohydrate 
• 108-94-1 cyclohexanone 
• 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 
• 83947-62-0 pinacol lithio(trimethylsilyl)methaneboronate 
• 74213-43-7 C₁₀H₂₂BO₂Si^(1-) 
• 72824-04-5 4,4,5,5-tetramethyl-2-(1-propenyl)-1,3,2-dioxaborolane 

Downstream Products

• 2043-61-0 cyclohexanecarbaldehyde 
• 7577-03-9 1-(cyclohexylidenemethyl)-4-methylbenzene 

Relevant academic research and scientific papers

Transition-Metal-Free Homologative Cross-Coupling of Aldehydes and Ketones with Geminal Bis(boron) Compounds

We report a transition-metal-free coupling of aldehydes and ketones with geminal bis(boron) building blocks which provides the coupled, homologated carbonyl compound upon oxidation. This reaction not only extends an alkyl chain containing a carbonyl group, it also simultaneously introduces a new carbonyl substituent. We demonstrate that enantiopure aldehydes with an enolizable stereogenic center undergo this reaction with complete retention of stereochemistry.

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

Cu-Catalyzed C-H Alkenylation of Benzoic Acid and Acrylic Acid Derivatives with Vinyl Boronates

An efficient Cu-catalyzed C-H alkenylation with acyclic and cyclic vinyl boronates was realized for the first time under mild conditions. The scope of the vinyl borons and the compatibility with functional groups including heterocycles are superior than Pd-catalyzed C-H coupling with vinyl borons, providing a reliable access to multisubstituted alkenes and dienes. Subsequent hydrogenation of the product from the internal vinyl borons will lead to installation of secondary alkyls.

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.

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.

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.

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.

Deprotonation of a Trimethylsilylmethaneboronic Ester

Deprotonation of pinacol trimethylsilymethaneboronate yields an anion which reacts with carbonyl compounds to form alkeneboronic esters, or with alkyl halides to form α-trimethylsilylalkaneboronic esters.