24488-80-0

Upstream product

• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 501-65-5 diphenyl acetylene 
• 24488-78-6 Z-1,2-bis(dichloroboryl)-1,2-di(phenyl)ethylene 
• 120-80-9 benzene-1,2-diol 

Relevant academic research and scientific papers

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.

Catalytic diboration of unsaturated molecules with platinum(0)-NHC: Selective synthesis of 1,2-dihydroxysulfones

Readily available N-heterocyclic platinum complexes provide active catalytic species for 1,2-diboration and anticipate a wide range of applications in alkenes and alkynes. Unprecedented catalytic B - B addition of heteroatom-containing sub-strates provided high selectivity into organosulfur - diboronate esters. Their in situ basic oxidation afforded the desired 1,2-dihydroxysulfones in high yields.

Synthesis and characterization of platinum(II)-Bis(boryl) catalyst precursors for diboration of alkynes and diynes: Molecular structures of cis-[(PPh3)2Pt(B-4-Butcat)2], cis-[(PPh3)2Pt(Bcat)2], cis-[(dppe)Pt(Bcat)2], cis-[(dppb)Pt(Bcat)2]

The reactions of the B-B-bonded compounds B2(cat)2 (cat = 1,2-O2C6H4) (1a), B2(4-But-cat)2 (1b), and B2(OCMe2CMe2O)2 (1c) with the Pt(0)-bis(phosphine) complex [(PPh3)2Pt(η-C2H4)] (4) via oxidative addition of the B-B bond yield cis-bis(boryl) Pt(II) complexes. The molecular structures of cis-[(PPh3)2Pt(Bcat)2]·C 6D6 (3a) and cis-[(PPh3)2Pt(B-4-Butcat)2] (3b) were determined by single-crystal X-ray diffraction. Reaction of 3a with 1 equiv of the bidentate phosphine dppe (Ph2PCH2CH2PPh2) or dppb (Ph2P(CH2)4PPh2) proceeds smoothly in toluene to give cis-[(dppe)Pt(Bcat)2] (5a) and cis-[(dppb)Pt(Bcat)2] (5b), respectively, which have also been characterized by X-ray diffraction. Compounds 3a,b and 4 are highly active catalyst precursors for the diboration of alkynes and 1,3-diynes. X-ray crystal structures of (E)-(4-MeOC6H4)C(Bcat)=CH(Bcat) (10c), (Z)-(C6H5)C(Bcat)=C(C6H5)(Bcat) (10e), and (Z,Z)-(4-MeOC6H4)C(Bcat)=C(Bcat)C(Bcat)=C(4-MeOC 6H4)(Bcat) (14a) confirm the cis stereochemistry of the boron substituents in three representative cases, namely, products of the catalyzed diboration of the terminal alkyne 4-MeOC6H4C=CH, the internal alkyne PhC=CPh, and the tetraboration of the diyne 4,4′-MeOC6H4C=CC=CC6H4OMe. The presence of the C=CSiMe3 moiety in catalytic reactions gives rise to additional products other than those derived from the diboration of the alkyne group. Metathetical reactions involving the diboron reagent and products derived from C-Si bond cleavage give rise to novel tris(boronate esters) as a result of the subsequent diboration of the C=CB(OR2) moieties formed by this competing process. The absence of catalytic activity using compound 5a, the extremely low activity of 5b, and the strong decrease in activity of 3b in the presence of added PPh3 suggests that phosphine dissociation is a critical step in the catalytic pathway.