100818-32-4Relevant articles and documents
β-Boration of α,β-unsaturated carbonyl compounds in ethanol and methanol catalyzed by CCC-NHC pincer Rh complexes
Reilly, Sean W.,Akurathi, Gopalakrishna,Box, Hannah K.,Valle, Henry U.,Hollis, T. Keith,Webster, Charles Edwin
, p. 32 - 38 (2016)
Quantitative β-boration of α,β-unsaturated carbonyl compounds was achieved utilizing the eco-friendly solvent EtOH along with MeOH at room temperature in 1 h, by a CCC-NHC pincer Rh complex mixture. Substrates with β-substituents were successfully convert
A borylcopper species generated from bis(pinacolato)diboron and its additions to α,β-unsaturated carbonyl compounds and terminal alkynes
Takahashi, Kou,Ishiyama, Tatsuo,Miyaura, Norio
, p. 47 - 53 (2001)
The addition of bis(pinacolato)diboron [(Me4C2O2)B-B(O2C2Me 4)] to α,β-unsaturated carbonyl compounds giving β-boryl carbonyl compounds and the addition to terminal alkynes yielding either 2-boryl-1-alkenes or 1-boryl-1-alkenes were carried out in DMF at room temperature in the presence of CuCl and AcOK. The transmetalation between diboron and [Cu(Cl)OAc]K generating a borylcopper species was proposed as the key step in the reactions because CuOAc similarly mediated both addition reactions to enones and alkynes in the presence of LiCl.
Addition and coupling reactions of bis(pinacolato)diboron mediated by CuCl in the presence of potassium acetate
Takahashi, Kou,Ishiyama, Tatsuo,Miyaura, Norio
, p. 982 - 983 (2000)
The addition of bis(pinacolato)diboron [(Me4C2O2)B-B(O2C2Me 4)] to α,β-unsaturated ketones, esters, nitriles, or terminal alkynes and the coupling with allyl chlorides were carried out in DMF at room temperature in the presence of CuCl and AcOK. The transmetalation from boron to copper generating a B-Cu species was proposed as the key step of the reactions.
Tandem β-boration/arylation of α,β-unsaturated carbonyl compounds by using a single palladium complex to catalyse both steps
Bonet, Amadeu,Gulyas, Henrik,Koshevoy, Igor O.,Estevan, Francisco,Sanau, Mercedes,Ubeda, M. Angeles,Fernandez, Elena
, p. 6382 - 6390 (2010)
Diphenyl(3-methyl-2-indolyl)phosphine (C9H8NPPh 2, 1) gives stable dimeric palladium(II) complexes that contain the phosphine in P,Nbridging coordination mode. On treating 1 with [Pd(O 2CCH3)2], the new complexes [Pd(μ-C 9H7NPPh2)-(NCCH3)]2 (2) or [Pd(μ-C9H7NPPh2)-(μ-O 2CCH3)]2 (3) were isolated, depending on the solvent used, acetonitrile or toluene, respectively. Further reaction of 3 with the ammonium salt of 1 led to the substitution of one carboxylate ligand to afford [Pd(u-C9H7NPPh2)3(μ-O 2CCH3)] (4), in which the bimetallic unit is bonded by three C9H7NPPh2- moieties and one carboxylate group. Using this methodology, [Pd2(μ-C 6H4PPh2)2(μ-C9H 7NPPh2)(μ-O2CCX3)] (X = H (7); J. = F (8)) were synthesised from the ortho-metalated compounds [Pd(C 6H4PPh2)(μO2CCX3)], (X = H (5); J. = F (6)). Complexes 3, 4, 7, and 8 have been found to be active in the catalytic β-boration of α,β-unsaturated esters and ketones under mild reaction conditions. Hindrance of the carbonyl moiety has an influence on the reaction rate, but quantitative conversion was achieved in many cases. More remarkably, when aryl bromides were added to the reaction media, complex 7 induced a highly successful consecutive β-boration/crosscoupling reaction with dimethyl acrylamide as the substrate (99% conversion, 89 % isolated yield).
Platinum catalysed 3,4- and 1,4-diboration of α,β-unsaturated carbonyl compounds using bis-pinacolatodiboron
Bell, Nathan J.,Cox, Andrew J.,Cameron, Neil R.,Evans, John S. O.,Marder, Todd B.,Duin, Marcel A.,Elsevier, Cornelis J.,Baucherel, Xavier,Tulloch, Arran A. D.,Tooze, Robert P.
, p. 1854 - 1855 (2004)
Bis-pinacolatodiboron reacts with α,β-unsaturated carbonyl compounds to give 1,4- and unprecedented 3,4-additions in the presence of a second generation Pt(0) catalyst at ambient temperature.
Sp2 - Sp3 hybridized mixed diboron: Synthesis, characterization, and copper-catalyzed β-boration of α,β- unsaturated conjugated compounds
Gao, Ming,Thorpe, Steven B.,Santos, Webster L.
, p. 3478 - 3481 (2009)
A novel sp2 - sp3 hybridized mixed diboron and its reactivity on the copper-catalyzed β-boration of α,β-unsaturated conjugated compounds to afford the corresponding β-borated compounds is reported. The presence of sp3-hybr
β-Borylation of conjugated carbonyl compounds with silylborane or bis(pinacolato)diboron catalyzed by Au nanoparticles
Fragkiadakis, Michael,Kidonakis, Marios,Stratakis, Manolis
, p. 8921 - 8927 (2020/11/23)
Conjugated aldehydes and ketones undergo reaction with Me2PhSiBpin (pin: pinacolato) catalyzed by Au nanoparticles supported on TiO2 forming exclusively the β-borylation products, via the intermediate formation of the labile silaboration adducts. This chemoselectivity pathway is complementary to the so far known analogous reaction catalyzed by other metals, where β-silylation occurs instead. β-Borylation also occurs with pinBBpin under identical reaction conditions in a variety of conjugated carbonyl compounds, including esters and amides which are unreactive in their attempted Au-catalyzed silaboration. This journal is
Structure and reactivity of a preactivated sp2-sp3 diboron reagent: Catalytic regioselective boration of α,β-unsaturated conjugated compounds
Gao, Ming,Thorpe, Steven B.,Kleeberg, Christian,Slebodnick, Carla,Marder, Todd B.,Santos, Webster L.
experimental part, p. 3997 - 4007 (2011/06/27)
A novel sp2-sp3 diboron reagent has been developed for the copper-catalyzed β-boration of α,β-unsaturated conjugated compounds. The reaction proceeds under mild conditions with various substrates, i.e., α,β-unsaturated esters, ketones, nitriles, ynones, amides, and aldehydes, in the absence of additives such as phosphine and sodium tert-butoxide to provide β-borylhomoenolates in good to excellent yields. The presence of an sp3-hybridized boron center, unambigously confirmed by X-ray crystallography, sufficiently activates the unsymmetrical pinacolato diisopropanolaminato diboron (PDIPA diboron, 2) to transfer the sp2-hybridized boron moiety chemoselectively. These observations suggest that the activation of one of the boron atoms is an essential step in the Cu-catalyzed β-boration catalytic cycle.
Suzuki-Miyaura cross-coupling of potassium trifluoroboratohomoenolates
Molander, Gary A.,Petrillo, Daniel E.
supporting information; experimental part, p. 1795 - 1798 (2009/04/10)
Ketone-, ester-, and amide-containing potassium trifluoroboratohomoenolates were prepared in good to excellent yields from the corresponding unsaturated carbonyl compounds. They were shown to be effective coupling partners in the Suzuki-Miyaura reaction with a variety of electrophiles including electron-rich and electron-poor aryl bromides and -chlorides.
