871125-68-7Relevant articles and documents
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
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
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
Creating High Regioselectivity by Electronic Metal-Support Interaction of a Single-Atomic-Site Catalyst
Jing, Hongyu,Li, Jiong,Li, Wen-Hao,Li, Yadong,Wang, Dingsheng,Wang, Yu,Yang, Jiarui,Zhang, Jian,Zhao, Jie
supporting information, p. 15453 - 15461 (2021/09/30)
Ligands are the most commonly used means to control the regioselectivity of organic reactions. It is very important to develop new regioselective control methods for organic synthesis. In this study, we designed and synthesized a single-atomic-site catalyst (SAC), namely, Cu1-TiC, with strong electronic metal-support interaction (EMSI) effects by studying various reaction mechanisms. π cloud back-donation to the alkyne on the metal catalytic intermediate was enhanced during the reaction by using transient electron-rich characteristics. In this way, the reaction achieved highly linear-E-type regioselective conversion of electronically unbiased alkynes and completely avoided the formation of branched isomers (ln:br >100:1, TON up to 612, 3 times higher than previously recorded). The structural elements of the SACs were designed following the requirements of the synthesis mechanism. Every element in the catalyst played an important role in the synthesis mechanism. This demonstrated that the EMSI, which is normally thought to be responsible for the improvement in catalytic efficiency and durability in heterogeneous catalysis, now first shows exciting potential for regulating the regioselectivity in homogeneous catalysis.
Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation
Tao, Lei,Guo, Xueying,Li, Jie,Li, Ruoling,Lin, Zhenyang,Zhao, Wanxiang
supporting information, p. 18118 - 18127 (2020/11/26)
The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.
Solvent- and metal-free hydroboration of alkynes under microwave irradiation
Arnaud, Alexandre,Doléans-Jordheim, Anne,Gioia, Bruna,Radix, Sylvie,Rocheblave, Luc,Walchshofer, Nadia
, (2020/01/22)
Boronic esters are versatile building blocks extensively used in organic chemistry and essential to a variety of coupling reactions. In this work, the hydroboration reactions of alkynes were performed without metal catalysts using concomitant microwave ir
Magnesium-Catalyzed Hydroboration of Terminal and Internal Alkynes
Magre, Marc,Maity, Bholanath,Falconnet, Alban,Cavallo, Luigi,Rueping, Magnus
supporting information, p. 7025 - 7029 (2019/04/26)
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
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
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
supporting information, p. 10821 - 10825 (2017/08/30)
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 alkenyl boronic esters from unfunctionalized alkenes: A boryl-heck reaction
Reid, William B.,Spillane, Jesse J.,Krause, Sarah B.,Watson, Donald A.
supporting information, p. 5539 - 5542 (2016/05/24)
We report the first example of a boryl-Heck reaction using an electrophilic boron reagent. This palladium-catalyzed process allows for the conversion of terminal alkenes to trans-alkenyl boronic esters using commercially available catecholchloroborane (catBCl). In situ transesterification allows for rapid access to a variety of boronic esters, amides, and other alkenyl boron adducts.
