581802-26-8Relevant articles and documents
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
Zirconium-Catalyzed Synthesis of Alkenylaminoboranes: From a Reliable Preparation of Alkenylboronates to a Direct Stereodivergent Access to Alkenyl Bromides
Birepinte, Mélodie,Chabaud, Laurent,Liautard, Virginie,Pucheault, Mathieu
, p. 2838 - 2843 (2020/04/16)
A simple procedure has been optimized for the preparation of alkenylaminoborane from alkynes using diisopropylaminoborane and HZrCp2Cl. Coupled with a magnesium-catalyzed dehydrogenation, it allowed for the use of air- and moisture-stable diisopropylamine. This synthesis has been extended to a one-pot sequence leading directly to bromoalkenes with controlled stereochemistry. As such, it provides an easy, scalable, cheap process to access alkenylboronates and both (E)- and (Z)-bromoalkenes from commercially available alkynes.
Synthesis of Alkenyl Boronates from Epoxides with Di-[B(pin)]-methane via Pd-Catalyzed Dehydroboration
Murray, Stephanie A.,Luc, Eugenia C. M.,Meek, Simon J.
supporting information, p. 469 - 472 (2018/01/28)
A practical and broadly applicable catalytic method for the synthesis of (E)-alkenylborons is presented. Reactions are promoted by [Pd(Cl)(η3-C3H5)]2 and proceed by the dehydroboration of cyclic borates. Through
Efficient heterogeneous hydroboration of alkynes: enhancing the catalytic activity by Cu(0) incorporated CuFe2O4 nanoparticles
Zeng, Xianghua,Gong, Chunhua,Guo, Haiyang,Xu, Hao,Zhang, Junyong,Xie, Jingli
supporting information, p. 17346 - 17350 (2018/11/01)
CuFe2O4 magnetic nanoparticles (NPs) are typically further calcined at high temperature to eliminate the reduced state of the Cu(0) source. Here we report the discovery of Cu(0) incorporated in CuFe2O4 that enables the catalytic activity for hydroboration of alkynes to be enhanced. This catalyst system has a low working temperature and short reacting time, and wide tolerance of substituted alkynes such as ynoate, ynamide and ynone. The Cu-CuFe2O4 catalyst was prepared by a simple hydrothermal method and well characterized by SEM, TEM, PXRD, XPS and EDS. Recycling of the catalyst was also achieved without obvious loss of activity after six runs. Furthermore, the mechanism of this reaction was also investigated.
Rhodium-Catalysed Hydroboration of Terminal Alkynes Using Pinacolborane Promoted by Tri(2-furyl)phosphine
Wang, Kongchen,Bates, Roderick W.
supporting information, p. 2749 - 2752 (2017/06/13)
Tri(2-furyl)phosphine is a superior ligand to triphenylphosphine in the rhodium-catalysed hydroboration of alkynes with pinacolborane to yield alkenylboronates. In general the reactions are faster and the products are cleaner.
Ligand-free hydroboration of alkynes catalyzed by heterogeneous copper powder with high efficiency
Zhao, Jie,Niu, Zhiqiang,Fu, Hua,Li, Yadong
supporting information, p. 2058 - 2060 (2014/03/21)
Regioselective hydroboration of terminal and internal alkynes is realized by using 10 mol% copper powder (0.3-1 μm) at room temperature. 24 alkynes were efficiently converted into vinylboronates in up to 96% yield without addition of any ligand or additiv
PtCl2/XPhos: A highly efficient and readily available catalyst for the hydrosilylation of propargylic alcohols
McLaughlin, Mark G.,Cook, Matthew J.
supporting information; experimental part, p. 11104 - 11106 (2011/11/07)
A highly regioselective hydrosilylation of propargylic alcohols has been developed using an in situ prepared PtCl2/XPhos catalyst system. The reaction is tolerant of many functional groups and exhibits excellent regio and geometric selectivity.
SN2′ boron-mediated Mitsunobu reactions - A new one-pot three-component synthesis of substituted enamides and enol benzoates
Berree, Fabienne,Gernigon, Nicolas,Hercouet, Alain,Chia, Hui Lin,Carboni, Bertrand
supporting information; experimental part, p. 329 - 333 (2009/07/04)
The conversion of (3-hydroxy-1-propen-1-yl)boronates to substituted enamides and enol benzoates is readily achieved in a one-pot procedure consisting of a regiocontrolled Mitsunobu reaction with convenient nucleophiles, followed by allylboration of aldehydes. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
Synthesis of functionalized vinyl boronates via ruthenium-catalyzed olefin cross-metathesis and subsequent conversion to vinyl halides
Morrill, Christie,Grubbs, Robert H.
, p. 6031 - 6034 (2007/10/03)
Functionalized vinyl pinacol boronates suitable for Suzuki cross-coupling reactions are synthesized using ruthenium-catalyzed olefin cross-metathesis of 1-propenyl pinacol boronate and various alkenes, including functionalized and 1,1-disubstituted alkenes. The resultant boronate cross products are stereoselectively transformed into predominantly Z-vinyl bromides and E-vinyl iodides. The vinyl bromides may be synthesized in a two-step, one-pot synthesis from a variety of olefins, resulting in a Z-selective formal vinyl bromide cross-metathesis reaction.