27826-44-4Relevant academic research and scientific papers
Efficient nickel/N-heterocyclic carbene catalyzed C-S cross-coupling
Guan, Pei,Cao, Changsheng,Liu, Yun,Li, Yunfei,He, Pan,Chen, Qian,Liu, Gang,Shi, Yanhui
supporting information, p. 5987 - 5992,6 (2012/12/12)
The cross-coupling reaction of aryl halides with aliphatic and aromatic thiols catalyzed by readily available Ni(OAc)2 with N-heterocyclic carbene (NHC) is reported. Ni(OAc)2/NHC catalyst showed good activities toward various aryl halides in C-S coupling reaction, even with aryl chlorides. Reactions occurred in excellent yields, broad scope, and high tolerance of functional groups.
Efficient nickel/N-heterocyclic carbene catalyzed C-S cross-coupling
Guan, Pei,Cao, Changsheng,Liu, Yun,Li, Yunfei,He, Pan,Chen, Qian,Liu, Gang,Shi, Yanhui
supporting information, p. 5987 - 5992 (2013/01/13)
The cross-coupling reaction of aryl halides with aliphatic and aromatic thiols catalyzed by readily available Ni(OAc)2 with N-heterocyclic carbene (NHC) is reported. Ni(OAc)2/NHC catalyst showed good activities toward various aryl halides in C-S coupling reaction, even with aryl chlorides. Reactions occurred in excellent yields, broad scope, and high tolerance of functional groups.
A kinetic investigation, supported by theoretical calculations, of steric and ring strain effects on the oxidation of sulfides and sulfoxides by dimethyldioxirane in acetone
Hanson, Peter,Hendrickx, Ramon A. A. J.,Lindsay Smith, John R.
supporting information; experimental part, p. 65 - 84 (2011/01/07)
The oxidations of alkyl 4-nitrophenyl, and dialkyl, sulfides and sulfoxides by dimethyldioxirane in acetone occur by concerted mechanisms but the sulfides respond differently from the sulfoxides to variation in the alkyl group. The reactions of the sulfides are inhibited by the steric effects of alkyl groups and these predominate over their inductive effects. By contrast, the reactions of these limited sets of sulfoxides are insensitive to alkyl steric effects but there is an indication of steric acceleration when a broader set of sulfoxides is considered. This behaviour is rationalised in terms of the differences in dipolar charge and its solvation between the ground state and transition state for the two types of substrate. The oxidations of cyclic sulfides and sulfoxides also exhibit contrasting behaviour. The reactivity of the sulfides is insensitive to ring strain but is explicable in frontier orbital terms whereas that of the sulfoxides is partly dependent upon the change in ring strain between reactant and product on oxidation, a difference rationalised in terms of the relative positions of the transition states in the reaction coordinates of the two oxidations. The reactivity of 4-, 5- and 6-membered cyclic sulfoxides is also dependent on a ring-size related property of the transition state. Calculations at the B3-LYP/6-31G* level of density functional theory on both ground states and transition states, including simulation of solvation by acetone, strongly support the mechanistic conclusions reached in this and earlier work.
Experimental verification of diverging mechanisms in the binding of ether, thioether, and sulfone ligands to a dirhodium tetracarboxylate
Mattiza, Jens T.,Meyer, Vera J.,Duddeck, Helmut
experimental part, p. 192 - 197 (2010/07/05)
Complexation of the oxygen atom in 2-butylphenylethers and sulfur in 2-butylphenylthioethers to a rhodium atom in dirhodium tetracarboxylate Rh (II)2[(R)-(+)-MTPA]4 is compared. Oxygen atoms complex via electrostatic attra
Alkylation of Several Nucleophiles with Alkylsulfonium Salts
Umemura, Kazuyuki,Matsuyama, Haruo,Kamigata, Nobumasa
, p. 2593 - 2600 (2007/10/02)
The reactions of dialkylphenylsulfonium salts (1) with several nucleophiles such as phenols, amine, enolate ion and thiolate ions, have been investigated.The relative reactivities of the alkyl groups of sulfonium salts for the phenolate ion (hard nucleophile) were as follows; Me:Et:i-Pr = 1.0:1.34:3.44.In the alkylation of the p-toluenethiolate ion (soft nucleophile) with 1, the opposite reactivity (Me:Et:i-Pr = 1.0:0.22:0.03) was found.When a sulfonium salt (1e) having an optically active (S)-s-butyl group was reacted with a phenolate ion, an optically active (R)-s-butyl phenyl ether was obtained with an inversion of the configuration at the chiral carbon atom.A reaction mechanism via a sulfurane intermediate is proposed for the alkylation of the phenolate ion with alkylsulfonium salts.The relative reactivities for the alkylation of several nucleophiles with dialkyl-phenylselenonium salts (12) were also investigated.
