215254-67-4

Upstream product

• 100-42-5 styrene 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 37737-62-5 tris(catecholato)diboron 
• 6783-04-6 (E)-2-(2'-phenylethenyl)-1,3,2-benzodioxaborole 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 536-74-3 phenylacetylene 

Downstream Products

• 93-56-1 phenylethane 1,2-diol 
• 189885-64-1 2,2'-(1-phenylethane-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 20273-74-9 2-(p-nitrophenyl)-1-phenylethanol 

Relevant academic research and scientific papers

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.

Palladium-NHC complexes do catalyse the diboration of alkenes: Mechanistic insights

Novel catalytic activation of the B-B bond by palladium(ii)-NHC complexes in presence of a mild base (NaOAc) and an excess of diboron reagent enables chemoselective 1,2-diboration of alkenes, suggesting the heterolytic cleavage of diboron rather than oxid

Developing a Bench-Scale Green Diboration Reaction toward Industrial Application

We report a new methodology for the organocatalytic diboration reaction using inexpensive, sustainable, nontoxic, commercially available halogen salts. This is an educative manuscript for the transformation of laboratory scale reactions into a sustainable approach of appeal to industry.

Amine Catalysis for the Organocatalytic Diboration of Challenging Alkenes

The generation of in situ sp2–sp3diboron adducts has revolutionised the synthesis of organoboranes. Organocatalytic diboration reactions have represented a milestone in terms of unpredictable reactivity of these adducts. However, current methodologies have limitations in terms of substrate scope, selectivity and functional group tolerance. Here a new methodology based on the use of simple amines as catalyst is reported. This methodology provides a completely selective transformation overcoming current substrate scope and functional/protecting group limitations. Mechanistic studies have been included in this report.

Dinuclear ortho-metalated palladium(II) compounds with N,N- and N,O-donor bridging ligands. synthesis of new palladium(III) complexes

New dinuclear ortho-metalated palladium(II) compounds with N,N′-diarylformamidinates, Pd2[(C6H 4)PPh2]2[R′NC(H)NR′]2 (R′ = C6H5, 3a; R′ = p-CH3C 6/sub

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.

A valuable, inexpensive CuIN-heterocyclic carbene catalyst for the selective diboration of styrene

The complexes [Cu(NHC)(NCMe)]BF4 (NHC = N-heterocyclic ligand), with bis(catecholato)diboron (B2(cat)2) as the boron source, efficiently catalyze the diboration of styrene with very high degrees of conversion. With the appropriate NHC ligand, the reaction proceeds quantitatively toward the diborated derivative PhCH(Bcat)-CH2(Bcat). The [styrene]/[B2(cat)2] ratio also has a strong effect on the selectivity: the use of an excess of styrene allows modification of the selectivity toward the formation solely of the monoborated derivative. PhCH 2-CH2(Bcat). DFT calculations suggest that no oxidative addition processes take place at copper, hut that intermediates containing coordinated σ-bonds are involved in the catalytic cycle.

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.