38199-89-2Relevant academic research and scientific papers
BH3 ? Me2S: An Alternative Hydride Source for NiH-Catalyzed Reductive Migratory Hydroarylation and Hydroalkenylation of Alkenes
Liu, Jiandong,Gong, Hegui,Zhu, Shaolin
supporting information, p. 1543 - 1546 (2021/03/03)
Borane dimethylsulfide (BMS) was found to be an efficient hydride source for nickel-hydride catalyzed reductive migratory hydrofunctionalization reactions. Catalytic reductive migratory hydroarylation and migratory hydroalkenylation were achieved with BMS in high yields and with excellent regioselectivity. A large-scale experiment employing as little as 0.5 equivalents of BH3 ? Me2S as the hydride source delivered the desired migratory hydroarylation product in high yield and selectivity.
Bidentate NHC-Cobalt Catalysts for the Hydrogenation of Hindered Alkenes
Wei, Zeyuan,Wang, Yujie,Li, Yibiao,Ferraccioli, Raffaella,Liu, Qiang
, p. 3082 - 3087 (2020/10/02)
Herein, we report a series of easily accessible bidentate N-heterocyclic carbene (NHC) cobalt catalysts, which enable the hydrogenation of hindered alkenes under mild conditions. The four-coordinated bidentate NHC-Co(II) complexes were characterized by X-ray diffraction, elemental analysis, ESI-HRMS, and magnetic moment measurements, revealing a distorted-tetrahedral geometry and a high-spin configuration of the metal center. The activity of the in situ formed catalytic system, which was obtained from easily available NHC precursors, CoCl2, and NaHBEt3, was identical with those of well-defined NHC-cobalt catalysts. This highlights the potential utility of this reaction system.
Bisoxazoline-pincer ligated cobalt-catalyzed hydrogenation of alkenes
Ritz, Mikhaila D.,Parsons, Astrid M.,Palermo, Philip N.,Jones, William D.
supporting information, (2020/02/13)
The efficient and atom economical hydrogenation of alkenes using a novel bisoxazoline ligated cobalt complex has been developed. The hydrogenation of a variety of alkenes containing electron neutral and electron-donating groups proceeds in high yield, whi
Gold-Catalyzed Friedel–Crafts-Like Reaction of Benzylic Alcohols to Afford 1,1-Diarylalkanes
Oakley, James V.,Stanley, Tyler J.,Jesse, Kate A.,Melanese, Amanda K.,Alvarez, Araceli A.,Prince, Aloha L.,Cain, Stephanie E.,Wenzel, Anna G.,Iafe, Robert G.
supporting information, p. 7063 - 7066 (2019/11/14)
A gold-catalyzed, Friedel–Crafts-like benzylation of unactivated benzylic alcohols to form 1,1-diarylalkanes has been developed. The operationally convenient method uses only 1.3 equivalents of the electron-rich arene, employs readily available starting m
Synthesis of 1-aryl- benzocycloalkane derivatives via one-pot two-step reaction of benzocyclonone, tosylhydrazide, and arylboronic acid
Liu, Shijuan,Fang, Meitong,Yin, Dongni,Wang, Yanan,Liu, Lei,Li, Xiuying,Che, Guangbo
, p. 942 - 949 (2019/03/14)
A metal-free one-pot two-step reductive coupling reaction of benzocyclonone, tosylhydrazide, and arylboronic acid was developed for the formation of a C(sp3)–C(sp2) bond, which enabled the efficient synthesis of 1-aryl-benzocycloalkane compounds in moderate to good yields on a multi-gram scale. Moreover, five- and six-membered benzocyclic ketones are also suitable substrates for this reaction. Notably, this protocol was also found to be suitable for synthesizing 3-(3,4-dichlorophenyl)-2,3-dihydro-1H-inden-1-one, an important intermediate in the synthesis of indatraline.
Air-Stable α-Diimine Nickel Precatalysts for the Hydrogenation of Hindered, Unactivated Alkenes
Léonard, Nadia G.,Chirik, Paul J.
, p. 342 - 348 (2018/01/17)
Treatment of a mixture of air-stable nickel(II) bis(octanoate), Ni(O2CC7H15)2, and α-diimine ligand, iPrDI or CyADI (iPrDI = [2,6-iPr2-C6H3N=C(CH3)]2, CyADI = [C6H11N=C(CH3)]2) with pinacolborane (HBPin) generated a highly active catalyst for the hydrogenation of hindered, essentially unfunctionalized alkenes. A range of tri- and tetrasubstituted alkenes was hydrogenated and a benchtop procedure for the hydrogenation of 1-phenyl-1-cyclohexene on a multigram scale was demonstrated and represents an advance in catalyst activity and scope for the nickel-catalyzed hydrogenation of this challenging class of alkenes. Deuteration of 1,2-dimethylindene with the in situ-generated nickel catalyst with iPrDI exclusively furnished the 1,2-syn-d2-dimethylindane. With cyclic trisubstituted alkenes, such as 1-methyl-indene and methylcyclohexene, deuteration with the in situ generated nickel catalyst under 4 atm of D2 produced multiple deuterated isotopologues of the alkanes, signaling chain running processes that are competitive with productive hydrogenation. Stoichiometric studies, titration, and deuterium labeling experiments identified that the borane reagent served the dual role of reducing nickel(II) bis(carboxylate) to the previously reported nickel hydride dimer [(iPrDI)NiH]2 and increasing the observed hydrogenation activity. Performing the catalyst activation procedure with D2 gas and HBPin generated both HD and DBPin, establishing that the borane is involved in H2 activation as judged by 1H and 11B nuclear magnetic resonance spectroscopies.
Mild and regioselective benzylic C-H functionalization: Ni-catalyzed reductive arylation of remote and proximal olefins
He, Yuli,Cai, Yalei,Zhu, Shaolin
supporting information, p. 1061 - 1064 (2017/05/15)
The synergistic combination of NiH-catalyzed alkene isomerization with nickel-catalyzed cross-coupling has yielded a general protocol for the synthesis of a wide range of structurally diverse 1,1-diarylalkanes in excellent yields and high regioselectivities from readily accessible olefin starting materials. Furthermore, the practicality and synthetic flexibility of this approach is highlighted by the successful employment of isomeric mixtures of olefins for regioconvergent arylation.
Room Temperature Catalyst System for the Hydroarylation of Olefins
Lee, Siu Yin,Villani-Gale, Alexander,Eichman, Chad C.
supporting information, p. 5034 - 5037 (2016/10/14)
A simple protocol for the hydroarylation of olefins to yield diarylmethine products is described. A Friedel-Crafts-type synthetic strategy allows direct access to biorelevant products in high atom efficiency. A combination of substoichiometric amounts of TMSCl and ZnBr2 promotes a rapid hydroarylation process at ambient temperature. The method is high yielding and is amenable to scale-up protocols.
H-β-zeolite-catalysed hydroarylation of styrenes
Mohan, Darapaneni Chandra,Patil, Rajendra D.,Adimurthy, Subbarayappa
experimental part, p. 3520 - 3525 (2012/07/30)
The hydroarylation of styrenes with various arene(heteroarene) compounds using H-β-zeolite as a green and recyclable heterogeneous catalyst under mild reaction conditions has been developed. The catalyst showed versatility and high selectivity (up to 100a€‰%) of desired 1,1-diarylalkanes in cyclohexane as solvent under the conditions studied. The catalyst could be reactivated by simple treatment with mineral acid at room temperature for better catalytic activity. Hydroarylation of styrenes with variousarene(heteroarene) compounds using H-β-zeolite as a green, heterogeneous and reusable catalyst under mild conditions is reported.
Efficient and general continuous-flow hydroarylation and hydroalkylation of styrenes
Rueping, Magnus,Bootwicha, Teerawut,Sugiono, Erli
experimental part, p. 2961 - 2965 (2011/02/22)
A simple and efficient continuous-flow hydroarylation of arenes and heteroarenes using various styrenes in conjunction with a heterogeneous catalyst has been developed. Additionally, this method has been successfully extended to the hydroalkylation of styrenes by employing 1,3-dicarbonyl compounds as the nucleophile. Multigram quantities of diarylmethanes have been prepared using this new flow method. Copyright
