82490-61-7Relevant academic research and scientific papers
Synthesis of 10-Methylsulfide and 10-Alkylmethylsulfonium nido-Carborane Derivatives: B–H···π Interactions between the B–H–B Hydrogen Atom and Alkyne Group in 10-RC≡CCH2S(Me)-7,8-C2B9H11
Anufriev, Sergey A.,Sivaev, Igor B.,Suponitsky, Kyrill Yu.,Godovikov, Ivan A.,Bregadze, Vladimir I.
, p. 4436 - 4443 (2017)
The 10-dimethylsulfonium derivative of nido-carborane 10-Me2S-7,8-C2B9H11 was prepared by reaction of the protonated form of nido-carborane with dimethylsulfide in toluene. Its partial demethylation with sodium amide in toluene gave the corresponding 10-methylsulfide derivative [10-MeS-7,8-C2B9H11]–. This 10-methylsulfide derivative was alkylated with various alkylating agents to produce a series of 10-alkylmethylsulfonium derivatives 10-R(Me)S-7,8-C2B9H11 (R = Et, Pr, Bu, CH2CH=CH2, CH2Ph, CH2C≡CH, CH2C≡CPh, CH2C≡CSiMe3). The 11B NMR spectra of the latter three compounds containing an acetylene group demonstrate unusually strong signal splitting that can be explained by strong intramolecular B–H···π(C≡C) interactions. The existence of such interactions in the solid state was supported by the X-ray crystal structure of 10-HC≡CCH2(Me)S-7,8-C2B9H11 with a short B–H···C(C≡C) distance of 2.658 ?. This is the first example of B–H···π(C≡C) hydrogen bonding.
Silver Mediated Banert Cascade with Carbon Nucleophiles
Alexander, Juliana R.,Kevorkian, Paul V.,Topczewski, Joseph J.
supporting information, p. 3227 - 3230 (2021/05/05)
The Banert cascade of propargylic azides can be promoted by simple silver salts, and the triazafulvene intermediate can be intercepted by carbon nucleophiles. Various indoles (>25 examples, up to 92% yield) and electron-rich heterocycles were effective. T
Intercepting the Banert cascade with nucleophilic fluorine: Direct access to α-fluorinated: N H-1,2,3-triazoles
Alexander,Kevorkian,Topczewski
supporting information, p. 5024 - 5027 (2021/05/28)
The treatment of propargylic azides with silver(i) fluoride in acetonitrile was found to yield α-fluorinated NH-1,2,3-triazoles via the Banert cascade. The reaction was regioselective and the products result from an initial [3,3] rearrangement. The reacti
Copper-Catalyzed Cross-Nucleophile Coupling of β-Allenyl Silanes with Tertiary C-H Bonds: A Radical Approach to Branched 1,3-Dienes
Shan, Qi-Chao,Hu, Lu-Min,Qin, Wei,Hu, Xu-Hong
supporting information, p. 6041 - 6045 (2021/08/03)
Described herein is a distinctive approach to branched 1,3-dienes through oxidative coupling of two nucleophilic substrates, β-allenyl silanes, and hydrocarbons appending latent functionality by copper catalysis. Notably, C(sp3)-H dienylation proceeded in a regiospecific manner, even in the presence of competitive C-H bonds that are capable of occurring hydrogen atom transfer process, such as those located at benzylic and other tertiary sites, or adjacent to an oxygen atom. Control experiments support the intermediacy of functionalized alkyl radicals.
Unbalanced-Ion-Pair-Catalyzed Nucleophilic Fluorination Using Potassium Fluoride
Hammond, Gerald B.,Li, Wangbing,Lu, Zhichao,Xu, Bo
supporting information, p. 9640 - 9644 (2021/12/14)
An unbalanced ion pair promoter (e.g., tetrabutylammonium sulfate), consisting of a bulky and charge-delocalized cation and a small and charge-localized anion, greatly accelerates nucleophilic fluorinations using easy handling KF. We also successfully converted an inexpensive and commercially available ion-exchange resin to the polymer-supported ion pair promoter (A26–SO42–), which could be reused after filtration. Moreover, A26–SO42– can be used in continuous flow conditions. In our conditions, water is well-tolerated.
Electrochemical Deoxygenative Thiolation of Preactivated Alcohols and Ketones
Zhang, Feng,Wang, Yang,Wang, Yi,Pan, Yi
supporting information, p. 7524 - 7528 (2021/10/02)
This work describes an electrochemically promoted nickel-catalyzed deoxygenative thiolation of alcohols and ketones under mild conditions. Excellent substrate tolerance and good chemical yields can be achieved by graphene/nickel foam electrodes in an undivided cell. Further study to gain mechanistic insight into this electrochemical cross-coupling has been carried out.
Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization
Powers, Zachary,Scharf, Adam,Cheng, Andrea,Yang, Feng,Himmelbauer, Martin,Mitsuhashi, Takaaki,Barra, Lena,Taniguchi, Yoshimasa,Kikuchi, Takashi,Fujita, Makoto,Abe, Ikuro,Porco, John A.
supporting information, p. 16141 - 16146 (2019/11/03)
A biomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)-derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical research communities. A concise synthetic route with the poten
Direct Access to Allenylphosphine Oxides via a Metal Free Coupling of Propargylic Substrates with P(O)H Compounds
Yang, Chun-Hua,Fan, Huihui,Li, Huimin,Hou, Shenyin,Sun, Xiangkun,Luo, Donghao,Zhang, Yinchao,Yang, Zhantao,Chang, Junbiao
, p. 9438 - 9441 (2019/11/20)
A direct and convenient approach for the coupling of propargylic substrates with diphenylphosphine oxide in the presence of Tf2O and 2,6-lutidine has been developed. The method provides a general approach for the construction of attractive allenylphosphoryl skeletons with high atom and step economy under metal free conditions.
Small molecular inhibitor realizing targeted combination of EGFR and EPS8 and application thereof
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Paragraph 0031; 0032; 0060; 0062; 0063; 0064, (2018/09/14)
The invention discloses a small molecular inhibitor EE02 realizing targeted combination of EGFR and EPS8 and application thereof. The small molecular inhibitor has a molecular formula of C44H54N4O6S,the molecular weight being 767, and the Chinese name of 1-{4-[4-(2-hydroxyl-3-{4-[(2Z)-3-phenylpropyl-2-alkene-1-yl]piperazidine-1-yl}propoxyl)phenylsulfonyl]phenoxyl}-3-{4-[(2Z)-3-phenylpropyl-2-alkene-1-yl]piperazidine-1-yl}-2-propanol. The small molecular inhibitor can effectively inhibit the multiplication of EGFR and EPS8 positive tumor, can be used for preparing medicine for treating EGFR and EPS8 positive tumor, and has great potential of being developed into anti-tumor small molecular targeted medicine.
One-Pot Synthesis of Polysubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Ag(I)-Catalyzed Cyclization/Isomerization
Xiong, Jun,Wei, Xiao,Liu, Zi-Ming,Ding, Ming-Wu
, p. 13735 - 13739 (2017/12/26)
A new one-pot preparation of polysubstituted imidazoles by a Staudinger/aza-Wittig/Ag(I)-catalyzed cyclization/isomerization has been developed. The easily accessible propargylazide derivatives reacted with triphenylphosphine, isocyanates, and amines sequ
