Efficient Monofluoroalkylation of Thiophenols or Phenols with α-Bromo-α-Fluoroketones under Mild Conditions

Synthesis ◽  
2021 ◽  
Author(s):  
Jingjing Wu ◽  
Fanhong Wu ◽  
Zhi Li ◽  
Mougui Fang ◽  
Yunli Liu ◽  
...  
Keyword(s):  
Phenolic Compounds ◽  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Functional Group ◽  
Nucleophilic Substitution Reaction ◽  
Mild Conditions ◽  
Broad Scope ◽  
Natural Phenolic Compounds

AbstractAn efficient nucleophilic substitution reaction between α-bromo-α-fluoroketones and thiophenols or phenols is reported for the synthesis of α-fluoro-β-ketosulfides or α-fluoro-β-ketone ethers in yields ranging from 78–93%. This method exhibits good functional group tolerance and a broad scope of nucleophilic substrates, including natural phenolic compounds.

A Brief Discussion on Nucleophilic Substitution Reaction on Saturated Carbon Atom

2013 ◽  
Vol 312 ◽  
pp. 433-437 ◽  
Author(s):  
Yan Ding
Keyword(s):  
Reaction Mechanism ◽  
Carbon Atom ◽  
Nucleophilic Substitution ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Substitution Reaction ◽  
Functional Group ◽  
Hydrolysis Reaction ◽  
Nucleophilic Substitution Reaction ◽  
Saturated Carbon Atom

Nucleophilic substitution reaction is an important reaction of haloalkane. By such a reaction, halogen functional group can turn into various other functional groups. Therefore, it is widely used in organic synthesis and there are many researches on its reaction mechanism. Hydrolysis reaction of bromoalkane is especially a nucleophilic substitution reaction that is studied quite fully. This paper mainly discusses the nucleophilic substitution reaction on saturated carbon atom.

Synthesis of Cyanamides from Cyanogen Bromide under Mild Conditions through N-Cyanation of Allylic Tertiary Amines

Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2675-2679 ◽  
Author(s):  
Chenghui Sun ◽  
Honggang Liang ◽  
Lingxiang Bao ◽  
Yao Du ◽  
Yiying Zhang ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Cyanogen Bromide ◽  
New Method ◽  
Nucleophilic Substitution Reaction ◽  
Tertiary Amines ◽  
Reaction Conditions ◽  
One Pot ◽  
Mild Conditions ◽  
One Step

Cyanamides were selectively formed through a one-step nucleophilic substitution reaction of allylic tertiary amines with cyanogen bromide. Because of the mild reaction conditions and good yields of the reaction, as well as the commercial availability of the starting materials, this new method represents a valuable tool for the synthesis of cyan­amides through an N-deallylation reaction and an N-cyanation reaction in one pot.

scholarly journals Iodine-catalyzed efficient synthesis of xanthene/thioxanthene-indole derivatives under mild conditions

RSC Advances ◽  
2020 ◽  
Vol 10 (42) ◽  
pp. 25165-25169
Author(s):  
Weihang Miao ◽  
Pingting Ye ◽  
Mengjiao Bai ◽  
Zhixin Yang ◽  
Suyue Duan ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Nucleophilic Substitution Reaction ◽  
Indole Derivatives ◽  
Efficient Synthesis ◽  
Mild Conditions

An efficient synthesis of xanthene/thioxanthene-indole derivatives has been developed through iodine-catalyzed nucleophilic substitution reaction of xanthen-9-ols and thioxanthen-9-ol with indoles.

scholarly journals Synthesis of Carbohydrate Based Macrolactones and Their Applications as Receptors for Ion Recognition and Catalysis

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3394
Author(s):  
Surya B. Adhikari ◽  
Anji Chen ◽  
Guijun Wang
Keyword(s):  
Nucleophilic Substitution ◽  
Supramolecular Chemistry ◽  
Copper Sulfate ◽  
Substitution Reaction ◽  
Biological Properties ◽  
Anion Binding ◽  
Nucleophilic Substitution Reaction ◽  
Binding Properties ◽  
Intramolecular Nucleophilic Substitution ◽  
Leaving Groups

Glycomacrolactones exhibit many interesting biological properties, and they are also important in molecular recognitions and for supramolecular chemistry. Therefore, it is important to be able to access glycomacrocycles with different sizes and functionality. A new series of carbohydrate-based macrocycles containing triazole and lactone moieties have been designed and synthesized. The synthesis features an intramolecular nucleophilic substitution reaction for the macrocyclization step. In this article, the effect of some common sulfonate leaving groups is evaluated for macrolactonization. Using tosylate gave good selectivity for monolactonization products with good yields. Fourteen different macrocycles have been synthesized and characterized, of which eleven macrocycles are from cyclization of the C1 to C6 positions of N-acetyl D-glucosamine derivatives and three others from C2 to C6 cyclization of functionalized D-glucosamine derivatives. These novel macrolactones have unique structures and demonstrate interesting anion binding properties, especially for chloride. The macrocycles containing two triazoles form complexes with copper sulfate, and they are effective ligands for copper sulfate mediated azide-alkyne cycloaddition reactions (CuAAC). In addition, several macrocycles show some selectivity for different alkynes.

Lewis-Acid-Catalyzed Direct Nucleophilic Substitution Reaction of Alcohols for the Functionalization of Aromatic Amines

2019 ◽  
Vol 4 (4) ◽  
pp. 1371-1374 ◽  
Author(s):  
Onkar S. Nayal ◽  
Maheshwar S. Thakur ◽  
Rohit Rana ◽  
Rahul Upadhyay ◽  
Sushil K. Maurya
Keyword(s):  
Nucleophilic Substitution ◽  
Lewis Acid ◽  
Aromatic Amines ◽  
Substitution Reaction ◽  
Nucleophilic Substitution Reaction ◽  
Acid Catalyzed
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