110-01-0Relevant articles and documents
Visible-Light-Promoted Oxo-difluoroalkylation of Alkenes with DMSO as the Oxidant
Xia, Zi-Hao,Gao, Zhong-Hua,Dai, Lei,Ye, Song
, p. 7388 - 7394 (2019)
Visible-light-promoted oxo-difluoroalkylation (acetylation and acetamidation) of alkenes with dimethyl sulfoxide as both the solvent and the oxidant was developed, affording the corresponding α,α-difluoro-?-ketoacetates and acetamides in modest yields. Both terminal and internal alkenes worked well for the reaction. This reaction features simple starting materials, a green oxidant, mild reaction conditions, and highly functional products.
The reactivity of (Me3Si)3SiH with sulfoxides under free radical conditions
Chatgilialoglu, Chryssostomos,Ferreri, Carla
, p. 7764 - 7769 (2016)
The radical-initiated reaction of (Me3Si)3SiH with a variety of sulfoxides has been investigated. The reactivity varies significantly with the nature of the starting materials. The reactions of diaryl sulfoxides provide the corresponding sulfides in high yields while the related reactions with dialkyl sulfoxides occur more slowly and in moderate yields. The rate constant for the addition of (Me3Si)3Si[rad] radical with dibutyl sulfoxide is in the range 103–104M?1s?1at 80 °C. The reactivity of (Me3Si)3SiH with 1,3-dithiolane derivatives has also been investigated in a comparative study. The 2,2-dimethyl-1,3-dithiolane and the corresponding 1,1-dioxide give very smooth reaction with (Me3Si)3Si[rad] radical attack at sulfur followed by the ring opening at S–CMe2bond and subsequent H-abstraction from the silane in very high yield, whereas the 2,2-dimethyl-1,3-dithiolane-1-oxide behaves quite differently and unexpectedly.
-
Olah et al.
, p. 4503 (1978)
-
-
Alper,Keung
, p. 53 (1970)
-
-
Nojima et al.
, p. 1343 (1975)
-
Synthesis, structure, and reactions of a copper-sulfido cluster comprised of the parent Cu2S unit: {(NHC)Cu}2(μ-S)
Zhai, Junjie,Filatov, Alexander S.,Hillhouse, Gregory L.,Hopkins, Michael D.
, p. 589 - 595 (2016)
The synthesis of the first CuI2(μ-S) complex, {(IPr?)Cu}2(μ-S) (IPr? = 1,3-bis(2,6-(diphenylmethyl)-4-methylphenyl)imidazol-2-ylidene; 1), has been accomplished via three synthetic routes: (1) salt metathesis between (IPr?)CuCl and Na2S; (2) silyl-deprotection reaction between (IPr?)Cu(SSiMe3) and (IPr?)CuF; and (3) acid-base reaction between (IPr?)Cu(SH) and (IPr?)Cu(OtBu). The X-ray crystal structure of 1 exhibits two two-coordinate copper centers connected by a bent Cu-S-Cu linkage. Application of these synthetic routes to analogous precursors containing the sterically smaller ligand IPr (1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidene), in place of IPr?, resulted in the formation of a transient product proposed as {(IPr)Cu}2(μ-S) (2), which decomposes quickly in solution. The instability of 2 probably results from the insufficient steric protection provided by IPr ligands to the unsaturated Cu2(μ-S) core; in contrast, 1 is stable both in solution and solid state for weeks. The nucleophilic sulfido ligand in 1 reacts with haloalkyl electrophiles (benzyl halides and dibromoalkanes) with formation of C-S bonds, affording (IPr?)Cu(SCH2Ph) and cyclic thioethers, respectively.
-
Johnson et al.
, p. 919 (1972)
-
Coenzyme F430 from Methanogenic Bacteria: Methane Formation by Reductive Carbon-Sulphur Bond Cleavage of Methyl Sulphonium Ions Catalysed by F430 Pentamethyl Ester
Jaun, Bernhard,Pfaltz, Andreas
, p. 293 - 294 (1988)
The nickel(I)-form of coenzyme F430 pentamethyl ester is an efficient catalyst for the reductive cleavage of methyl sulphonium salts to methane and thioesters.
Efficient reduction of sulfoxides with 2,6-dihydroxypyridine
Miller, Samantha J.,Collier, Talia R.,Wu, Weiming
, p. 3781 - 3783 (2000)
2,6-Dihydroxypyridine was found to be an efficient reagent in the deoxygenation of sulfoxides. The mild reaction conditions were compatible with functional groups such as ester and carbamate. It was also found that approximately 0.25 equivalents of 2,6-dihydroxypyridine was required for effective reduction. (C) 2000 Elsevier Science Ltd.
Catalytic dehydrogenation of amines to imines and the in-situ reduction of sulfoxides into sulfides
Li, Bo,Liu, Bing,Liu, Xixi,Wang, Wei,Wang, Yanxin,Xiang, Nian,Zhang, Zehui
, p. 81 - 88 (2021/07/30)
The catalytic acceptorless dehydrogenation of primary amines into imines and H2 represents one of the most important organic transformations, and the in-situ utilization of the generated H2 for chemical reduction reactions has never
Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale
Mayer, Robert J.,Hampel, Nathalie,Ofial, Armin R.
supporting information, p. 4070 - 4080 (2021/01/29)
A quantitative Lewis acidity/basicity scale toward boron-centered Lewis acids has been developed based on a set of 90 experimental equilibrium constants for the reactions of triarylboranes with various O-, N-, S-, and P-centered Lewis bases in dichloromethane at 20 °C. Analysis with the linear free energy relationship log KB=LAB+LBB allows equilibrium constants, KB, to be calculated for any type of borane/Lewis base combination through the sum of two descriptors, one for Lewis acidity (LAB) and one for Lewis basicity (LBB). The resulting Lewis acidity/basicity scale is independent of fixed reference acids/bases and valid for various types of trivalent boron-centered Lewis acids. It is demonstrated that the newly developed Lewis acidity/basicity scale is easily extendable through linear relationships with quantum-chemically calculated or common physical–organic descriptors and known thermodynamic data (ΔH (Formula presented.)). Furthermore, this experimental platform can be utilized for the rational development of borane-catalyzed reactions.
Nickel phosphide nanoalloy catalyst for the selective deoxygenation of sulfoxides to sulfides under ambient H2pressure
Fujita, Shu,Mitsudome, Takato,Mizugaki, Tomoo,Yamaguchi, Sho,Yamasaki, Jun,Yamazoe, Seiji
supporting information, p. 8827 - 8833 (2020/11/23)
Exploring novel catalysis by less common, metal-non-metal nanoalloys is of great interest in organic synthesis. We herein report a titanium-dioxide-supported nickel phosphide nanoalloy (nano-Ni2P/TiO2) that exhibits high catalytic activity for the deoxygenation of sulfoxides. nano-Ni2P/TiO2 deoxygenated various sulfoxides to sulfides under 1 bar of H2, representing the first non-noble metal catalyst for sulfoxide deoxygenation under ambient H2 pressure. Spectroscopic analyses revealed that this high activity is due to cooperative catalysis by nano-Ni2P and TiO2. This journal is
