1073354-88-7Relevant articles and documents
Magnesium-Catalyzed Hydroboration of Terminal and Internal Alkynes
Magre, Marc,Maity, Bholanath,Falconnet, Alban,Cavallo, Luigi,Rueping, Magnus
, p. 7025 - 7029 (2019)
A magnesium-catalyzed hydroboration of alkynes providing good yields and selectivities for a wide range of terminal and symmetrical and unsymmetrical internal alkynes has been developed. The compatibility with many functional groups makes this magnesium c
Cyclodextrin Cavity-Induced Mechanistic Switch in Copper-Catalyzed Hydroboration
Zhang, Pinglu,Meijide Suárez, Jorge,Driant, Thomas,Derat, Etienne,Zhang, Yongmin,Ménand, Micka?l,Roland, Sylvain,Sollogoub, Matthieu
, p. 10821 - 10825 (2017)
N-heterocyclic carbene-capped cyclodextrin (ICyD) ligands, α-ICyD and β-ICyD derived from α- and β-cyclodextrin, respectively give opposite regioselectivities in a copper-catalyzed hydroboration. The site-selectivity results from two different mechanisms: the conventional parallel one and a new orthogonal mechanism. The shape of the cavity was shown not only to induce a regioselectivity switch but also a mechanistic switch. The scope of interest of the encapsulation of a reactive center is therefore broadened by this study.
Direct Synthesis of Alkenylboronates from Alkenes and Pinacol Diboron via Copper Catalysis
Lu, Wenkui,Shen, Zengming
supporting information, p. 142 - 146 (2019/01/11)
We report an efficient approach for the direct synthesis of alkenylboronates using copper catalysis. The Cu/TEMPO catalyst system (where TEMPO = (2,2,6,6-tetramethylpiperidin-1-yl)oxyl) exhibits both excellent reactivity and selectivity for the synthesis of alkenylboronates, starting from inexpensive and abundant alkenes and pinacol diboron. This approach allows for the direct functionalization of both aromatic and aliphatic terminal alkenes. Mechanistic experiments suggest that the alkenylboronates arise from oxyboration intermediates.
Selective and efficient synthesis of trans-arylvinylboronates and trans-hetarylvinylboronates using palladium catalyzed cross-coupling
Liu, Zhihao,Wei, Wei,Xiong, Lu,Feng, Qiang,Shi, Yaojie,Wang, Ningyu,Yu, Luoting
supporting information, p. 3172 - 3176 (2017/04/14)
trans-Arylvinylboronate derivatives are important synthesis blocks in natural products, pharmaceuticals and organic materials. There are only a few reaction conditions that could selectively provide trans-arylvinylboronates by Heck coupling of pinacol vin
Soluble Platinum Nanoparticles Ligated by Long-Chain N-Heterocyclic Carbenes as Catalysts
Martínez-Prieto, Luis M.,Rakers, Lena,López-Vinasco, Angela M.,Cano, Israel,Coppel, Yannick,Philippot, Karine,Glorius, Frank,Chaudret, Bruno,van Leeuwen, Piet W. N. M.
supporting information, p. 12779 - 12786 (2017/09/06)
Soluble platinum nanoparticles (Pt NPs) ligated by two different long-chain N-heterocyclic carbenes (LC-IPr and LC-IMe) were synthesized and fully characterized by TEM, high-resolution TEM, wide-angle X-ray scattering (WAXS), X-ray photoelectron spectrosc
Highly selective methods for synthesis of internal (α-) vinylboronates through efficient NHC-Cu-catalyzed hydroboration of terminal alkynes. Utility in chemical synthesis and mechanistic basis for selectivity
Jang, Hwanjong,Zhugralin, Adil R.,Lee, Yunmi,Hoveyda, Amir H.
, p. 7859 - 7871 (2011/06/27)
Cu-catalyzed methods for site-selective hydroboration of terminal alkynes, where the internal or α-vinylboronate is generated predominantly (up to >98%) are presented. Reactions are catalyzed by 1-5 mol % of N-heterocyclic carbene (NHC) complexes of copper, easily prepared from N-aryl-substituted commercially available imidazolinium salts, and proceed in the presence of commercially available bis(pinacolato)diboron [B2(pin)2] and 1.1 equiv of MeOH at -50 to -15 °C in 3-24 h. Propargyl alcohol and amine and the derived benzyl, tert-butyl, or silyl ethers as well as various amides are particularly effective substrates; also suitable are a wide range of aryl-substituted terminal alkynes, where higher α-selectivity is achieved with substrates that bear an electron-withdrawing substituent. α-Selective Cu-catalyzed hydroborations are amenable to gram-scale procedures (1 mol % catalyst loading). Mechanistic studies are presented, indicating that α selectivity arises from the structural and electronic attributes of the NHC ligands and the alkyne substrates. Consistent with suggested hypotheses, catalytic reactions with a Cu complex, derived from an N-adamantyl-substituted imidazolinium salt, afford high β selectivity with the same class of substrates and under similar conditions.