53367-02-5Relevant academic research and scientific papers
Transition-Metal-Free Sulfuration/Annulation of Alkenes: Economical Access to Thiophenes Enabled by the Cleavage of Multiple C-H Bonds
Chen, Liang,Min, Hao,Zeng, Weilan,Zhu, Xiaoming,Liang, Yun,Deng, Guobo,Yang, Yuan
supporting information, p. 7392 - 7395 (2019/01/03)
A novel, atom economical, and transition-metal-free strategy for the synthesis of thiophenes from substituted buta-1-enes with potassium sulfide has been presented. The reaction achieves double C-S bond formations via cleavage of multiple C-H bonds and provides an efficient approach to access various functionalized thiophenes. Moreover, the strategy can also be used for the synthesis of thiophenes from 1,4-diaryl-1,3-dienes. Mechanistically, DMSO plays a role of oxidant and S3?- in situ generated from K2S is involved.
One-pot synthesis of 1,3-diaryl but-1-enes from 1-arylethanols over Snβ zeolite
Mameda, Naresh,Gajula, Krishna Sai,Peraka, Swamy,Kodumuri, Srujana,Chevella, Durgaiah,Banothu, Rammurthy,Amrutham, Vasu,Nama, Narender
, p. 95 - 99 (2016/12/09)
An environmentally benign catalytic protocol has been successfully developed for the one-pot synthesis of 1,3-diaryl but-1-enes from 1-arylethanols via dehydration of 1-arylethanols followed by head-to-tail dimerization of vinylarenes over heterogeneous c
Bimetallic nanosized solids with acid and redox properties for catalytic activation of C-C and C-H bonds
Cabrero-Antonino, Jose R.,Tejeda-Serrano, María,Quesada, Manuel,Vidal-Moya, Jose A.,Leyva-Pérez, Antonio,Corma, Avelino
, p. 689 - 696 (2016/12/28)
A new approach is presented to form self-supported bimetallic nanosized solids with acid and redox catalytic properties. They are water-, air- and H2-stable, and are able to activate demanding C-C and C-H reactions. A detailed mechanistic study on the formation of the Ag-Fe bimetallic system shows that a rapid redox-coupled sequence between Ag+, O2 (air) and Fe2+ occurs, giving monodisperse Ag nanoparticles supported by O-bridged diatomic Fe3+ triflimides. The system can be expanded to Ag nanoparticles embedded within a matrix of Cu2+, Bi3+ and Yb3+ triflimide.
A novel efficient method for the synthesis of substituted olefins; Cross coupling of two different alcohols using NaHSO4/SiO2
Aoyama, Tadashi,Koda, Shuichi,Takeyoshi, Yuka,Ito, Tetsuhiro,Takido, Toshio,Kodomari, Mitsuo
, p. 6605 - 6607 (2013/07/26)
Simple and efficient cross coupling of alcohols was developed in the presence of NaHSO4/SiO2 to give the corresponding substituted olefins. Direct coupling of alcohols and alkenes was also achieved to give substituted olefins. NaHSO4/SiO2 could be recycled 7 times without loss of catalytic activity.
Pd-catalyzed π-chelation assisted ortho-C-H activation and annulation of allylarenes with internal alkynes
Gandeepan, Parthasarathy,Cheng, Chien-Hong
supporting information, p. 2084 - 2087 (2013/06/05)
The synthesis of highly substituted naphthalenes from allylarenes and alkynes is described. This reaction proceeds via π-coordination of an allylic carbon-carbon double bond to the Pd(II) center and is followed by ortho selective C-H bond activation.
Iron(III) triflimide as a catalytic substitute for gold(I) in hydroaddition reactions to unsaturated carbon-carbon bonds
Cabrero-Antonino, Jose R.,Leyva-Perez, Antonio,Corma, Avelino
supporting information, p. 8627 - 8633 (2013/07/26)
In this work it is shown that iron(III) and gold(I) triflimide efficiently catalyze the hydroaddition of a wide array of nucleophiles including water, alcohols, thiols, amines, alkynes, and alkenes to multiple C-C bonds. The study of the catalytic activity and selectivity of iron(III), gold(I), and Bronsted triflimides has unveiled that iron(III) triflimide [Fe(NTf 2)3] is a robust catalyst under heating conditions, whereas gold(I) triflimide, even stabilized by PPh3, readily decomposes at 80 °C and releases triflimidic acid (HNTf2) that can catalyze the corresponding reaction, as shown by in situ 19F, 15N, and 31P NMR spectroscopy. The results presented here demonstrate that each of the two catalyst types has weaknesses and strengths and complement each other. Iron(III) triflimide can act as a substitute of gold(I) triflimide as a catalyst for hydroaddition reactions to unsaturated carbon-carbon bonds. Lewis and Bronsted catalysis: It is shown that iron(III) catalyses as efficiently as gold(I) the hydroaddition of a wide array of nucleophiles, including water, alcohols, thiols, amines, alkynes, and alkenes, to multiple C-C bonds (see scheme). Copyright
Iron-catalysed Markovnikov hydrothiolation of styrenes
Cabrero-Antonino, Jose R.,Leyva-Perez, Antonio,Corma, Avelino
, p. 678 - 687 (2012/04/18)
The bis(triflimide)iron(III) salt catalyzes the hydrothiolation of styrenes in a Markovnikov fashion with good selectivities and high yields. After isolation, different benzylic thioethers are obtained. This iron(III) catalyst is unique in terms of regioselectivity and represents a sustainable and economic alternative to those processes based on stoichiometric reagents. Copyright
In(OTf)3-catalyzed highly chemo- and regioselective head-to-tail heterodimerization of vinylarenes with 1,1-diarylethenes
Dai, Jing,Wu, Jinlong,Zhao, Guanglian,Dai, Wei-Min
supporting information; experimental part, p. 8290 - 8293 (2011/08/10)
Cross combination: The olefinic C-H bond in 1,1-diarylethenes selectively adds to the C=C double bond of substituted styrenes in a head-to-tail fashion under In(OTf)3 (OTf=triflate) catalysis (see scheme) while homo- and cyclodimerization reactions are suppressed. The high chemo- and regioselectivity of this intermolecular hydroalkenylation originates from the high stability and steric bulk of the diaryl-substituted tertiary carbocation intermediate. Copyright
A new type of carbonylation of styrenes catalyzed by Pd(OAc)2 combined with molybdovanadophosphate
Yamada, Shingo,Obora, Yasushi,Sakaguchi, Satoshi,Ishii, Yasutaka
experimental part, p. 1194 - 1198 (2009/06/06)
A new type of carbonylation of styrenes was achieved under a 1:1 mixture of CO (0.5 atm) and O2 (0.5 atm) in the presence of Pd(OAc)2 combined with H5PMo10V2O40 nH 2O to give 4-methyl-2-phenylnaphthalen-1(4H)-one in 78% yield. Various substituted styrenes were also carbonylated to the corresponding substituted arylnaphthalen-l(4H)-ones in moderate yields. The reaction was found to proceed in two stages involving the head-to-tail dimerization of styrenes, followed by carbonylation of the resulting dimers. Styrenes were efficiently dimerized under air (1 atm) in the absence of CO even at room temperature to produce head-to-tail dimers in good yields.
