2263-73-2Relevant academic research and scientific papers
Metal-free oxidative coupling of alkyl chlorides with thiols: An efficient access to sulfoxides
Liu, Qian,Zhao, Xiaoqian,Xu, Feng,Li, Gaoqiang
supporting information, (2019/12/27)
An efficient and step-economical access to sulfoxides from thiols and alkyl halides in the presence of I2O5 and DBU via direct oxidative couplings is described here. It is the first case that combined Williamson sulfide synthesis and subsequent sulfide oxidation into one step manipulation for sulfoxides preparation. This protocol features wide substrate scope, mild and metal-free conditons, the use of naturally abundant starting materials and avoidance of over-oxidation.
Method of preparing sulfoxide compounds from benzyl chloride compound and thiophenol by one-step reaction in metal free condition
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Paragraph 0066; 0067; 0068; 0069, (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.
Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications
Wang, Lei,Chen, Mingjie,Zhang, Peichao,Li, Wenbo,Zhang, Junliang
, p. 3467 - 3473 (2018/03/13)
Herein we reported an efficient palladium-catalyzed enantioselective arylation of both alkyl and aryl sulfenate anions to deliver various chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos). PC-Phos are easily prepared in short steps from inexpensive commercially available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered ring was formed via the O,P-coordination with the palladium(II) center. The salient features of this method include general substrate scope, ease of scale-up, applicable to the late-stage modification of bioactive compounds, and the synthesis of a marketed medicine Sulindac.
A route to benzylic arylsulfoxides from β-ketosulfoxides
Chang, Meng-Yang,Cheng, Yu-Chieh,Chan, Chieh-Kai
, p. 4068 - 4075 (2016/07/06)
The K2CO3-mediated benzylation of β-ketosulfoxides 4 with 2.0?equiv of benzylic halides 5 affords benzylic arylsulfoxides 6 in moderate yields along with trace amounts of chalcones 7. The products 6 are assumed to form in situ intermediates of sulfenate anions from β-ketosulfoxides which are commonly involved in carbon–sulfur bond formation. A plausible mechanism has been proposed.
Palladium-Catalyzed Arylation of Alkyl Sulfenate Anions
Jia, Tiezheng,Zhang, Mengnan,Jiang, Hui,Wang, Carol Y.,Walsh, Patrick J.
, p. 13887 - 13893 (2016/01/15)
A unique palladium-catalyzed arylation of alkyl sulfenate anions is introduced that affords aryl alkyl sulfoxides in high yields. Due to the base sensitivity of the starting sulfoxides, sulfenate anion intermediates, and alkyl aryl sulfoxide products, the use of a mild method to generate alkyl sulfenate anions was crucial to the success of this process. Thus, a fluoride triggered elimination strategy was employed with alkyl 2-(trimethylsilyl)ethyl sulfoxides to liberate the requisite alkyl sulfenate anion intermediates. In the presence of palladium catalysts with bulky monodentate phosphines (SPhos and Cy-CarPhos) and aryl bromides or chlorides, alkyl sulfenate anions were readily arylated. Moreover, the thermal fragmentation and the base promoted elimination of alkyl sulfoxides was overridden. The alkyl sulfenate anion arylation exhibited excellent chemoselectivity in the presence of functional groups, such as anilines and phenols, which are also known to undergo palladium catalyzed arylation reactions.
Synthesis of sulfur-bridged polycycles via Pd-catalyzed dehydrogenative cyclization
Wang, Binjie,Liu, Yue,Lin, Cong,Xu, Yiming,Liu, Zhanxiang,Zhang, Yuhong
supporting information, p. 4574 - 4577 (2015/01/08)
A general approach to sulfur-bridged polycycles by palladium-catalyzed double C(sp2)-H bond oxidative cyclization is presented. This protocol afforded diverse sulfur-bridged five-, six-, and seven-membered polycycles in moderate to good yields with a tolerance for a wide variety of functional groups. A sulfide-bridged six-membered pyrene-thienoacene compound was synthesized readily using this method, and excellent performance for photoluminescence quantum yield was observed.
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
