1242770-51-9Relevant articles and documents
Lithium diisobutyl-: Tert-butoxyaluminum hydride (LDBBA) catalyzed hydroboration of alkynes and imines with pinacolborane
Jaladi, Ashok Kumar,Kim, Hanbi,Lee, Ji Hye,Shin, Won Kyu,Hwang, Hyonseok,An, Duk Keun
, p. 16524 - 16529 (2019)
Lithium diisobutyl-tert-butoxyaluminum hydride (LDBBA)-catalyzed hydroboration of alkynes with pinacolborane (HBpin) was demonstrated. The hydroboration proceeded more efficiently with LDBBA than with other aluminum hydrides and afforded alkenyl boronates in moderate to good yields. In addition, high-yielding LDBBA-catalyzed hydroboration of imines was achieved. The coordination of anionic aluminate with lithium enables effective hydride transfer for hydroboration.
An Effective Catalytic Hydroboration of Alkynes in Supercritical CO2 under Repetitive Batch Mode
Szyling, Jakub,Franczyk, Adrian,Stefanowska, Kinga,Klarek, Mateusz,Maciejewski, Hieronim,Walkowiak, J?drzej
, p. 531 - 539 (2018)
A facile method for the synthesis of unsaturated organoboron compounds by hydroboration of terminal and internal alkynes in supercritical (sc) CO2 has been presented for the first time. The reactions performed in scCO2 in the presence of Ru catalysts (selectivity, productivity) are compared with those in a traditionally used solvent or without it. Moreover, the catalytic systems based on the application of scCO2 have been successfully tested for the processes under repetitive batch conditions. This strategy permitted us to obtain boryl-substituted olefins with high yields and selectivities up to the 16th catalytic cycle if using Ru(CO)Cl(H)(PPh3)3 as a catalyst. The process applied the self-dosing catalyst, which is gradually released to the reaction mixture under supercritical conditions in the individual batch. Such an approach has a positive impact on process sustainability and economy.
Neosilyllithium-Catalyzed Hydroboration of Alkynes and Alkenes in the Presence of Pinacolborane (HBpin)
Kumar, Gobbilla Sai,Moorthy, Shruti,Karmakar, Himadri,Singh, Saurabh Kumar,Panda, Tarun K.
supporting information, (2021/11/13)
We report here a novel protocol for the hydroboration of alkynes and alkenes, which in the presence of neosilyllithium (LiCH2SiMe3) (5 mol %) and pinacolborane efficiently results in the formation of corresponding alkenyl and alkyl b
Highly efficient hydroboration of alkynes catalyzed by porous copper-organic framework under mild conditions
Gao, Ning,Hu, Tianding,Kang, Xiaomin,Lan, Xingwang,Wang, Zhenguang,Wu, Zhi-Lei,Zhao, Bin
, p. 250 - 257 (2021/10/25)
The hydroboration of alkynes is crucial due to the wide applications in organic synthesis, while such reaction is often completed with low turnover frequency (TOF) value and long reaction time. Therefore, it is very important and necessary that the hydrob
Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes
Zhong, Mingbing,Gagné, Yohann,Hope, Taylor O.,Pannecoucke, Xavier,Frenette, Mathieu,Jubault, Philippe,Poisson, Thomas
supporting information, p. 14498 - 14503 (2021/05/21)
The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B2Pin2 permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and a
Selective hydroboration of alkynes via multisite synergistic catalysis by PCN-222(Cu)
Ma, L. J.,Tang, Z. Y.,Yuan, J. C.,Zhang, L. J.,Zhang, X. M.
, p. 63 - 69 (2021/08/03)
Zirconium-based porphyrinic MOFs (PMOFs, MOF = metal-organic framework) have gained considerable attention in the field of electric/thermo/photo-catalysis as heterogeneous single-site catalysts; however, the study on multisite synergistic catalysis of PMO
Electrochemical Hydroboration of Alkynes
Aelterman, Maude,Jubault, Philippe,Poisson, Thomas,Sayes, Morgane
supporting information, p. 8277 - 8282 (2021/05/27)
Herein we reported the electrochemical hydroboration of alkynes by using B2Pin2 as the boron source. This unprecedented reaction manifold was applied to a broad range of alkynes, giving the hydroboration products in good to excellent yields without the need of a metal catalyst or a hydride source. This transformation relied on the possible electrochemical oxidation of an in situ formed borate. This anodic oxidation performed in an undivided cell allowed the formation of a putative boryl radical, which reacted on the alkyne.
Cs4B4O3F10: First Fluorooxoborate with [BF4] Involving Heteroanionic Units and Extremely Low Melting Point
Xia, Ming,Mutailipu, Miriding,Li, Fuming,Yang, Zhihua,Pan, Shilie
supporting information, p. 9753 - 9757 (2021/05/27)
Herein, a new congruently melting mixed-anion compound Cs4B4O3F10 has been characterized as the first fluorooxoborate with [BF4] involving heteroanionic units. Compound Cs4B4O3F10 possesses two highly fluorinated anionic clusters and therefore its formula can be expressed as Cs3(B3O3F6) ? Cs(BF4). The influence of [BF4] units on micro-symmetry and structural evolution was discussed based on the parent compound. More importantly, Cs4B4O3F10 shows the lowest melting point among all the available borates and thus sets a new record for such system. This work is of great significance to enrich and tailor the structure of borates using perfluorinated [BF4] units.
Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies
Mai, Binh Khanh,Nguyen, Thanh Vinh,Ton, Nhan N. H.
, p. 9117 - 9133 (2021/07/19)
Hydroboration reaction of alkynes is one of the most synthetically powerful tools to access organoboron compounds, versatile precursors for cross-coupling chemistry. This type of reaction has traditionally been mediated by transition-metal or main group catalysts. Herein, we report a novel method using tropylium salts, typically known as organic oxidants and Lewis acids, to promote the hydroboration reaction of alkynes. A broad range of vinylboranes can be easily accessed via this metal-free protocol. Similar hydroboration reactions of alkenes and epoxides can also be efficiently catalyzed by the same tropylium catalysts. Experimental studies and DFT calculations suggested that the reaction follows an uncommon mechanistic pathway, which is triggered by the hydride abstraction of pinacolborane with tropylium ion. This is followed by a series ofin situcounterion-activated substituent exchanges to generate boron intermediates that promote the hydroboration reaction.
Cobalt-Catalyzed Hydroboration of Terminal and Internal Alkynes
González, María J.,Bauer, Felix,Breit, Bernhard
supporting information, p. 8199 - 8203 (2021/10/25)
A novel methodology to access synthetically versatile vinylboronic esters through a ligand-controlled cobalt-catalyzed hydroboration of terminal and internal alkynes is reported. The approach relies on the in situ reduction of Co(II) by H-BPin in the presence of bisphosphine ligands generating catalytically active Co(I) hydride complexes. This procedure avoids the use of stoichiometric amounts of base, and no boron-containing byproducts are generated which is translated into high functional group tolerance and atom economy.
