180746-15-0Relevant academic research and scientific papers
Method of preparing sulfoxide compounds from benzyl chloride compound and thiophenol by one-step reaction in metal free condition
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Paragraph 0018; 0019; 0020; 0021, (2019/04/06)
The invention discloses a method of preparing sulfoxide compounds from benzyl chloride compound and thiophenol by a one-step reaction in a metal free condition. The method can be used for preparing aseries of sulfoxide compounds in a mild condition by taking benzyl chloride compound and thiophenol as reaction raw materials, iodine pentoxide as an oxidizing agent and 1,8-diazabicycloundecylenic-7-ene as alkali with a high yield. By taking halogenated hydrocarbon and thiol as reactants directly, compared with known and popular methods of generating thioether by halogenated hydrocarbon and thiolunder the action of strong alkali, separating a thioether compound and oxidizing the thioether to synthesize sulfoxide through an oxidizing agent, the reaction steps are shortened to one step from two steps. The middle treatment process of the reaction is few, the atom economy is good, and no transitional metal catalysts take part in the reaction, so that the synthetic cost is low, the reaction condition is mild, and the method opens up a novel and efficient path which is high in atom economy and low in cost for preparing the sulfoxide compounds and has a wide application prospect.
Nondirected Copper-Catalyzed Sulfoxidations of Benzylic C-H Bonds
Yu, Hao,Li, Zhen,Bolm, Carsten
supporting information, p. 2076 - 2079 (2018/04/16)
A copper-catalyzed sulfoxidation of benzylic C-H bonds by nondirected oxidative C(sp3)-H activation was developed. The process proceeds via sulfenate anions, which are generated by base-triggered elimination of β-sulfinyl esters and benzyl radicals. The functional group tolerance is high, and the product yields are good.
Copper-catalyzed asymmetric oxidation of sulfides
O'Mahony, Graham E.,Ford, Alan,Maguire, Anita R.
body text, p. 3288 - 3296 (2012/05/20)
Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of th
Aryl(chloro)methyl 4-tolyl sulfoxides: Synthesis and application to the synthesis of α-aryl ketones
Fukuda, Shigehiko,Tsuji, Kazuhito,Musashi, Jun,Nonaka, Ryo,Kimura, Tsutomu,Satoh, Tsuyoshi
experimental part, p. 3615 - 3626 (2011/12/16)
Aryl(chloro)methyl 4-tolyl sulfoxides were synthesized from arylmethyl 4-tolyl sulfoxides in moderate-to-good yields by sequential treatment with lithium diisopropylamide and tosyl chloride at low temperatures. Treatment of the lithium α-sulfinyl carbanion of the aryl(chloro)methyl 4-tolyl sulfoxides with aldehydes or ketones resulted in the formation of adducts in good-to-high yields. Treatment of these adducts with tert-butylmagnesium chloride gave the corresponding magnesium alkoxides. On treatment with isopropylmagnesium chloride, the alkoxides gave the corresponding magnesium β-oxido carbenoids, which rearranged to give α-aryl ketones in good-to-high yields. The magnesium enolate intermediates generated by rearrangement of the -oxido carbenoids could also be trapped with electrophiles to give α-aryl α-substituted ketones. These procedures offer a good method for the synthesis of a variety of α-aryl ketones from aldehydes and ketones. Georg Thieme Verlag Stuttgart. New York.
Asymmetric synthesis of aryl benzyl sulfoxides by vanadium-catalysed oxidation: A combination of enantioselective sulfide oxidation and kinetic resolution in sulfoxide oxidation
Kelly, Padraig,Lawrence, Simon E.,Maguire, Anita R.
, p. 4500 - 4509 (2007/10/03)
Enantioselective vanadium-catalysed oxidation of aryl benzyl sulfides using Bolm's procedure is accompanied by kinetic resolution in the oxidation of the resulting sulfoxides which enhances the enantiopurities of the sulfoxides recovered (typically >90% ee), albeit with an associated reduction in yield. The effects of ligand, solvent and reaction conditions are discussed in detail. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
A novel method for the stereoselective synthesis of tetralins and indanes
Appelbe, Zelda,Casey, Mike,Keaveney, Claire M.,Kelly, Cornelius J.
, p. 1404 - 1408 (2007/10/03)
Heavily-substituted 1-aryltetralins and 1-arylindanes were prepared in a highly stereoselective manner using a two-step sequence. Addition of t-butyl benzyl sulfoxides to unsaturated carbonyl compounds gave conjugate adducts with high diastereoselectivity
