Aluminum(III) Chloride Promoted Oxygen Transfer: Selective Oxidation of Sulfides to Sulfoxides

Synlett ◽  
2017 ◽  
Vol 29 (03) ◽  
pp. 340-343 ◽  
Author(s):  
Zhengming Li ◽  
Yongtao Xie ◽  
Yuxin Li ◽  
Sha Zhou ◽  
Shaa Zhou ◽  
...  
Keyword(s):  
Selective Oxidation ◽  
Lewis Acid ◽  
Oxygen Transfer ◽  
Functional Group ◽  
High Efficiency ◽  
Mild Conditions ◽  
Oxidation Of Sulfides

An efficient selective oxidation of sulfides to sulfoxides has been developed by means of AlCl3-promoted oxygen transfer from phenyliodine diacetate [PhI(OAc)2]. AlCl3 proved to be the optimal ­Lewis acid for the activation of PhI(OAc)2. Various substituted sulfides were selectively transformed into the corresponding sulfoxides in good to excellent yields (≤99%). The high efficiency, excellent functional-group compatibility, broad substrate scope, and mild conditions render the current transformation useful for the synthesis of sulfoxides.

Nickel-Catalyzed Reductive Monofluoroakylation of Alkyl Tosylate with Bromofluoromethane to Access Primary Alkyl Fluoride

2021 ◽  
Author(s):  
Ru Cui ◽  
Jie Sheng ◽  
Bing-Bing Wu ◽  
Duo-Duo Hu ◽  
Hong-Qian Zheng ◽  
...  
Keyword(s):  
Functional Group ◽  
High Efficiency ◽  
Low Cost ◽  
Raw Material ◽  
Mild Conditions

A nickel-catalysed direct terminal monofluormethlyation between alkyl tosylates and a low-cost, industrial raw material bromofluoromethane has been developed. This transformation has demonstrated high efficiency, mild conditions, and good functional-group compatibility....

scholarly journals Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN2 pincer ligand

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xingjie Zhang ◽  
Di Qi ◽  
Chenchen Jiao ◽  
Xiaopan Liu ◽  
Guisheng Zhang
Keyword(s):  
Functional Group ◽  
High Efficiency ◽  
Materials Science ◽  
Alkylating Agents ◽  
Sonogashira Coupling ◽  
Pincer Ligand ◽  
One Pot ◽  
Mild Conditions ◽  
Alkyl Amines ◽  
Sonogashira Reactions

AbstractAlkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Here, we show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts. Key to the success of this coupling is the development of an easily accessible and bench-stable amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions, and produces diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrate scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals.

Efficient Synthesis of Diverse 5-Thio- or 5-Selenotriazoles: One-Pot Multicomponent Reaction from Elemental Sulfur or Selenium

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4170-4182 ◽  
Author(s):  
Lin-Lin Zhang ◽  
Ya-Ting Li ◽  
Ting Gao ◽  
Sha-Sha Guo ◽  
Bei Yang ◽  
...  
Keyword(s):  
Elemental Sulfur ◽  
Functional Group ◽  
High Efficiency ◽  
Efficient Synthesis ◽  
One Pot ◽  
Mild Conditions ◽  
Ligand Free ◽  
Multistep Reaction ◽  
Easy Operation

A sequential multistep reaction toward 5-thio- or 5-selenotriazoles has been established by generation of both copper(I) triazolides and sulfenylating or selenylating agents in situ, starting from elemental sulfur or selenium. This reaction features mild conditions, readily available and broad-scope substrates, good functional group compatibility, high efficiency and regioselectivity, easy operation, and ligand-free CuI.

Lewis Acid-Mediated Efficient Synthesis of 4H-1,3-benzo-xazines and Their Derivatives 4,5-dihydro-1,3-benzo-xazepines

2020 ◽  
Vol 24 (11) ◽  
pp. 1263-1273
Author(s):  
An Junkai ◽  
Liu Jikun ◽  
Shi Ying ◽  
Zhu Weiwei ◽  
Guo Guoying ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Lewis Acid ◽  
Functional Group ◽  
Materials Science ◽  
Pharmaceutical Research ◽  
Direct Access ◽  
Efficient Synthesis ◽  
Mild Conditions ◽  
Promising Strategy ◽  
Characteristic Features

: Compounds containing 4H-1,3-benzo-xazine core usually possess characteristic features and have been applied in the fields of organic synthesis, pharmaceutical research, materials science and bioscience. Here we reported convenient and direct access to 4H-1,3- benzo-xazines and their derivatives through intramolecular cyclization of olefinic amides or ureas with good to excellent yields in the presence of TMSOTf. The properties (mild conditions, metal or additives-free, wide substrate scope and functional group tolerance) of the process made it a promising strategy to synthesize various benzo-xazines and their derivatives.

3-Carboxypyridinium chlorochromate – aluminium chloride — An efficient and inexpensive reagent system for the selective oxidation of sulfides to sulfoxides and sulfones in solution and under microwave irradiation

2005 ◽  
Vol 83 (2) ◽  
pp. 115-121 ◽  
Author(s):  
Iraj Mohammadpoor-Baltork ◽  
Hamid R Memarian ◽  
Kiumars Bahrami
Keyword(s):  
Microwave Irradiation ◽  
Functional Groups ◽  
Selective Oxidation ◽  
Lewis Acid ◽  
Aluminium Chloride ◽  
Double Bonds ◽  
Oxidation Of Sulfides ◽  
Efficient Reagent

3-Carboxypyridinium chlorochromate (CPCC) in the presence of aluminium chloride is a very efficient reagent for the selective oxidation of sulfides to sulfoxide and sulfones in solution and under microwave irradiation. It is noteworthy that different functional groups including carbon–carbon double bonds, ketones, oximes, aldehydes, ethers, and acetals were tolerated under these reaction conditions.Key words: sulfoxides, sulfones, oxidation, chlorochromate, Lewis acid.

Sulfuryl Fluoride Promoted Thiocyanation of Alcohols: A Practical Method for Preparing Thiocyanates

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1413-1417
Author(s):  
Chengrong Ding ◽  
Guofu Zhang ◽  
Lidi Xuan ◽  
Yiyong Zhao
Keyword(s):  
Ethyl Acetate ◽  
Functional Group ◽  
High Efficiency ◽  
Bond Cleavage ◽  
Ammonium Thiocyanate ◽  
Practical Method ◽  
Sulfuryl Fluoride ◽  
Mild Conditions ◽  
One Step ◽  
The One

A novel SO2F2-promoted thiocyanation method for the one-step synthesis of thiocyanates through C–O bond cleavage of readily available alcohols with ammonium thiocyanate as the thiocyanating agent was developed. The method avoids the use of additional catalyst, and a variety of (hetero)arene, alkene and aliphatic alcohols reacted with high efficiency in ethyl acetate under mild conditions to afford the corresponding thiocyanates in excellent to quantitative yields with broad functional-group compatibility.

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