948595-14-0

Upstream product

• 695-12-5 vinylcyclohexane 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 

Downstream Products

• 61414-09-3 1-cyclohexylethane-1,2-diol 

Relevant academic research and scientific papers

Unprecedented use of silver(I) N-heterocyclic carbene complexes for the catalytic preparation of 1,2-bis(boronate) esters

Catalytic diboration of internal and terminal alkenes with Ag(I) N-heterocyclic carbene complexes leads to 1,2-bis(boronate) esters as single intermediates, that can be oxidised towards the corresponding diols. The Royal Society of Chemistry 2005.

Transition-metal-free diboration reaction by activation of diboron compounds with simple lewis bases

Changing behavior: A nucleophilic sp2 carbene-type boryl moiety, formed upon interaction of tetraalkoxydiboranes and a Lewis base, can attack non-activated C=C bonds. Computational studies identify the interaction as the overlap between the strongly polarized B-B σ bond (HOMO) and the antibonding πorbital (LUMO) of the C=C bond. Conceptually, the normally electrophilic boron becomes nucleophilic and forces the olefin to act as an electrophile. Copyright

Gold(0) nanoparticles for selective catalytic diboration

Going with gold: Gold(0) nanoparticles stabilized with the diphosphine ligand binap mediate the catalytic diboration of styrene, resulting in complete formation of the bis(boronate)ester product. The gold(0) catalytic mechanism can involve base-assisted h

Multifaceted palladium catalysts towards the tandem diboration-arylation reactions of alkenes

Novel Pd26+ compounds have been synthesized in high yield. These compounds and their Pd24+ counterparts as synthetic precursors mediate the diboration of vinylarenes and aliphatic 1-alkenes, and under mild and basic reaction conditions they produce a variety of 1,2-diboronate esters with excellent conversions and chemo-selectivities. The presence of bis(catecholato)diboron (B2cat2) favours the reduction of PdIII to PdII, while the catalytic precursor of PdII is transformedinto Pd0-nanoparticles. An "in situ" catalytic tandem reaction has been designed to transform the diboronate intermediates into the monoarylated product, which after oxidative workup, provides the carbohydroxylated adduct. Eventually, the same catalyst performs both sequences with total conversion from the alkene.

Enantioselective preparation of a chiral-at-metal Cp*Ir(NHC) complex and its application in the catalytic diboration of olefins

The reaction of(S,S)-1,3-di(methylbenzyl)imidazolium chloride with [Cp*IrCl2]2 in the presence of NaOAc affords the diastereoselective formation of a Cp*Ir(NHC) complex with a chelating ligand coordinated through the carbene and the

Coinage metal complexes with N-heterocyclic carbene ligands as selective catalysts in diboration reaction

We describe the improved catalytic reactivity of terminal alkenes with 1,2-diboranes in the presence of Au(I) and Ag(I) complexes when N-heterocyclic carbene ligands are used. The new catalytic systems are able to diminish the undesired β-H-elimination of the alkylboryl-metal intermediates, which leads to the formation of hydroborated byproducts. The electronic properties and molecular the structure of the precursors of the catalysts could explain the modest asymmetric induction provided.

Regioselective homologation of bis(boronate) intermediates derived from rhodium-catalyzed diboration of simple alkenes

Regioselective homologation of alkyl-1,2-bis(catecholboronates) may be accomplished by treatment of these reactive intermediates with TMSCHN 2. A convenient process is reported where alkene diboration and the subsequent homologation reaction are accomplished in the same reaction flask. Georg Thieme Verlag Stuttgart.