126688-99-1Relevant articles and documents
Catalytic Enantioselective Synthesis of anti-Vicinal Silylboronates by Conjunctive Cross-Coupling
Kong, Ziyin,Meng, Yan,Morken, James P.
, p. 8456 - 8459 (2020)
Chiral 1,2-bimetallic reagents are useful motifs in synthetic chemistry. Although syn-1,2-bimetallic compounds can be prepared by alkene dimetallation, anti-1,2-bimetallics are still rare. The stereospecific 1,2-metallate shift that occurs during conjunctive cross-coupling is shown to enable a practical and modular approach to the catalytic synthesis of enantioenriched anti-1,2-borosilanes. In addition to reaction development, the synthetic utility of anti-1,2-borosilanes was investigated, including applications to the synthesis of anti-1,2-diols and anti-1,2-amino alcohols.
Aluminum-Catalyzed Selective Hydroboration of Nitriles and Alkynes: A Multifunctional Catalyst
Sarkar, Nabin,Bera, Subhadeep,Nembenna, Sharanappa
, p. 4999 - 5009 (2020/05/01)
The reaction of LH [L = {(ArNH)(ArN)-C=N-C=(NAr)(NHAr)}; Ar =2,6-Et2-C6H3] with a commercially available alane amine adduct (H3Al·NMe2Et) in toluene resulted in the formation of a conjugated bis-guanidinate (CBG)-supported aluminum dihydride complex, i.e., LAlH2 (1), in good yield. The new complex has been thoroughly characterized by multinuclear magnetic resonance, IR, mass, and elemental analyses, including single-crystal structural studies. Further, we have demonstrated the aluminum-catalyzed hydroboration of a variety of nitriles and alkynes. Moreover, aluminum-catalyzed hydroboration is expanded to more challenging substrates such as alkene, pyridine, imine, carbodiimide, and isocyanides. More importantly, we have shown that the aluminum dihydride catalyzed both intra- A nd intermolecular chemoselective hydroboration of nitriles and alkynes over other reducible functionalities for the first time.
Cu-Catalyzed C-H Alkenylation of Benzoic Acid and Acrylic Acid Derivatives with Vinyl Boronates
Li, Jian-Jun,Wang, Cheng-Gang,Yu, Jin-Feng,Wang, Peng,Wang, Peng,Yu, Jin-Quan
supporting information, p. 4692 - 4696 (2020/06/25)
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.
Aluminium complex-catalysed hydroboration of alkenes and alkynes
Harinath, Adimulam,Banerjee, Indrani,Bhattacharjee, Jayeeta,Panda, Tarun K.
supporting information, p. 10531 - 10536 (2019/07/09)
We demonstrate an efficient method for the hydroboration of terminal alkenes or alkynes with pinacolborane (HBpin) using the aluminium catalyst, [κ2-{Ph2P(=Se)NCH2(C5H4N)}Al(CH3)2/sub
Tris(2,4,6-trifluorophenyl)borane: An Efficient Hydroboration Catalyst
Lawson, James R.,Wilkins, Lewis C.,Melen, Rebecca L.
supporting information, p. 10997 - 11000 (2017/08/22)
The metal-free catalyst tris(2,4,6-trifluorophenyl)borane has demonstrated its extensive applications in the 1,2-hydroboration of numerous unsaturated reagents, namely alkynes, aldehydes and imines, consisting of a wide array of electron-withdrawing and donating functionalities. A range of over 50 borylated products are reported, with many reactions proceeding with low catalyst loading under ambient conditions. These pinacol boronate esters, in the case of aldehydes and imines, can be readily hydrolyzed to leave the respective alcohol and amine, whereas alkynyl substrates result in vinyl boranes. This is of great synthetic use to the organic chemist.
Lewis acid catalysis: Catalytic hydroboration of alkynes initiated by Piers' borane
Fleige, Mirco,M?bus, Juri,Vom Stein, Thorsten,Glorius, Frank,Stephan, Douglas W.
supporting information, p. 10830 - 10833 (2016/09/09)
Terminal and internal alkynes are efficiently hydroborated to (E)-alkenyl pinacol boronic esters with excellent yields and selectivities using a Lewis acid catalyst. In the case of Piers' borane (HB(C6F5)2) the borane acts as a pre-catalyst generating dissymmetrically gem-diborylated species of the form RCH2CR′(Bpin)(B(C6F5)2) which are the active catalysts.
Copper-catalyzed monoborylation of silylalkynes; Regio- and stereoselective synthesis of (Z)-β-(borylvinyl)silanes
Chae, Yeong Mi,Bae, Jun Sung,Moon, Jong Hun,Lee, Jin Yong,Yun, Jaesook
supporting information, p. 843 - 849 (2014/04/03)
The selective copper-catalyzed borylation of silylalkynes in the presence of a diboron reagent and methanol produced a variety of (Z)-β-(borylvinyl) silanes. The appropriate use of a selective ligand for copper allows the chemo-, regio-, and stereoselective monoborylation of silylalkynes. The β-regioselectivity of an N-heterocyclic carbene (NHC)-copper catalyst was investigated by DFT calculations.
Di(isopropylprenyl)borane: A new hydroboration reagent for the synthesis of alkyl and alkenyl boronic acids
Kalinin, Alexey V.,Scherer, Stefan,Snieckus, Victor
, p. 3399 - 3404 (2007/10/03)
The best of the old: The new hydroboration reagent 1 combines the selectivity of disiamylborane (2) with the reactivity towards carbonyls of allyl boranes 3. Conventional oxidative workup conditions are avoided, as facile hydrolysis in protic media provides the corresponding boronic acids with up to 99% anti-Markovnikov selectivities. A one-pot hydroboration/ Suzuki-Miyaura protocol adds to the synthetic value of 1.
