Synthesis of 2-trifluoromethyl indoles via visible-light induced intramolecular radical cyclization

RSC Advances ◽  
2015 ◽  
Vol 5 (49) ◽  
pp. 39625-39629 ◽  
Author(s):  
Xichang Dong ◽  
Yumin Hu ◽  
Tiebo Xiao ◽  
Lei Zhou
Keyword(s):  
Visible Light ◽  
Formation Process ◽  
Bond Formation ◽  
Radical Cyclization ◽  
Mild Conditions ◽  
Rapid Construction

A visible-light induced intramolecular radical cyclization is described. The reaction allows the rapid construction of 2-trifluoromethyl-3-acylindoles in a sequential C–C and C–O bond formation process under mild conditions.

Visible-Light-Promoted Radical Cyclization of N-Arylvinylsulfonamides: Synthesis of CF3/CHF2/CH2CF3-Containing 1,3-Dihydrobenzo[c]isothiazole 2,2-Dioxide Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Devaiah Vytla ◽  
Kumargurubaran Kaliyaperumal ◽  
Rajeswari Velayuthaperumal ◽  
Parinita Shaw ◽  
Raj Gautam ◽  
...  
Keyword(s):  
Visible Light ◽  
Radical Cyclization ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Reaction Proceeds ◽  
High Yields

AbstractA photocatalyzed and highly efficient trifluoromethylation of N-arylvinylsulfonamides using commercially available CF3SO2Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild conditions. An investigation of the substrate scope is performed to establish a general, synthetically useful protocol for the synthesis of novel trifluoromethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in moderate to high yields. This method is also successfully applied for the synthesis of difluoromethylated and trifluoroethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in good to excellent yields.

Metal-free n-Et4NBr-catalyzed radical cyclization of disulfides and alkynes leading to benzothiophenes under mild conditions

RSC Advances ◽  
2014 ◽  
Vol 4 (89) ◽  
pp. 48547-48553 ◽  
Author(s):  
Daoshan Yang ◽  
Kelu Yan ◽  
Wei Wei ◽  
Laijin Tian ◽  
Qinghe Li ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Bond Formation ◽  
Environmentally Friendly ◽  
Radical Cyclization ◽  
Title Reaction ◽  
Metal Free ◽  
Mild Conditions

The title reaction involves metal free TEAB-catalyzed S–S bond cleavage, C–S bond formation and C–C bond formation; it uses readily available disulfides and alkynes as substrates, and environmentally friendly TEAB as catalyst to synthesize useful benzothiophene derivatives.

Efficient photocatalytic chemoselective and stereoselective C–C bond formation over AuPd@N-rich carbon nitride

2021 ◽  
Author(s):  
Heyan Jiang ◽  
Jie Xu ◽  
Sishi Zhang ◽  
Hongmei Cheng ◽  
Cuicui Zang ◽  
...  
Keyword(s):  
Visible Light ◽  
Heck Reaction ◽  
Carbon Nitride ◽  
Bond Formation ◽  
Reaction Products ◽  
Mild Conditions ◽  
Light Color

High unsymmetrical chemoselective Ullmann biaryl products and satisfactory Z-type stereoselective Heck reaction products could be achieved through changing the visible light color over AuPd@N-Rich carbon nitride under mild conditions.

Visible Light Photocatalyzed Carbon-Heteroatom Bond Formation and Synthesis of Related Compounds

2017 ◽  
Vol 3 (4) ◽  
pp. 279-317 ◽  
Author(s):  
Nirmalya Mukherjee ◽  
Pintu Maity ◽  
Tubai Ghosh ◽  
Subir Panja ◽  
Brindaban C. Ranu
Keyword(s):  
Visible Light ◽  
Bond Formation ◽  
Related Compounds

Enantioselective Radical Functionalization of Imines and Iminium Intermediates via Visible Light Photoredox Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Jia-Jia Zhao ◽  
Hong-Hao Zhang ◽  
Shouyun Yu
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Asymmetric Reduction ◽  
Chemical Transformations ◽  
Photoredox Catalysis ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Iminium Ions ◽  
Radical Functionalization

Visible light photoredox catalysis has recently emerged as a powerful tool for the development of new and valuable chemical transformations under mild conditions. Visible-light promoted enantioselective radical transformations of imines and iminium intermediates provide new opportunities for the asymmetric synthesis of amines and asymmetric β-functionalization of unsaturated carbonyl compounds. In this review, the advance in the catalytic asymmetric radical functionalization of imines, as well as iminium intermediates, are summarized. 1 Introduction 2 The enantioselective radical functionalization of imines 2.1 Asymmetric reduction 2.2 Asymmetric cyclization 2.3 Asymmetric addition 2.4 Asymmetric radical coupling 3 The enantioselective radical functionalization of iminium ions 3.1 Asymmetric radical alkylation 3.2 Asymmetric radical acylation 4 Conclusion

scholarly journals Continuous-Flow Processes for the Production of Floxacin Intermediates: Efficient C–C Bond Formation through a Rapid and Strong Activation of Carboxylic Acids

2020 ◽  
Vol 02 (03) ◽  
pp. e128-e132
Author(s):  
Shao-Zheng Guo ◽  
Zhi-Qun Yu ◽  
Wei-Ke Su
Keyword(s):  
Reaction Time ◽  
Continuous Flow ◽  
Flow System ◽  
Bond Formation ◽  
Product Yield ◽  
Raw Material ◽  
Material Consumption ◽  
Tank Reactor ◽  
Mild Conditions ◽  
Flow Processes

AbstractThe development of highly efficient C–C bond formation methods for the synthesis of ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-(dimethylamino)acrylate 1 in continuous flow processes has been described, which is based on the concept of rapid and efficient activation of carboxylic acid. 2,4-Dichloro-5-fluorobenzoic acid is rapidly converted into highly reactive 2,4-dichloro-5-fluorobenzoyl chloride by treating with inexpensive and less-toxic solid bis(trichloromethyl)carbonate. And then it rapidly reacts with ethyl 3-(dimethylamino)acrylate to afford the desired 1. This process can be performed under mild conditions. Compared with the traditional tank reactor process, less raw material consumption, higher product yield, less reaction time, higher operation safety ensured by more the environmentally friendly procedure, and process continuity are achieved in the continuous-flow system.

Visible-Light-Mediated Tandem Sulfonylation/Cyclization of Vinyl Azides with Sulfonyl Hydrazines for the Synthesis of 6-(Sulfonylmethyl)phenanthridines under Mild Conditions

Synlett ◽  
2019 ◽  
Vol 30 (08) ◽  
pp. 955-960 ◽  
Author(s):  
Liu-Liang Mao ◽  
Li-Xia Quan ◽  
Xian-Hong Zhu ◽  
Cong-Bin Ji ◽  
An-Xi Zhou ◽  
...  
Keyword(s):  
Visible Light ◽  
Mild Conditions ◽  
Simple Strategy ◽  
Vinyl Azides

A visible-light-mediated tandem sulfonylation/cyclization of vinyl azides with sulfonyl hydrazines was developed that provides an efficient and simple strategy for the synthesis of valuable 6-(sulfonylmethyl)phenanthridines with a broad substrate scope and satisfactory yields under mild conditions.

Visible light-photocatalysed carbazole synthesis via a formal (4+2) cycloaddition of indole-derived bromides and alkynes

2016 ◽  
Vol 52 (29) ◽  
pp. 5128-5131 ◽  
Author(s):  
Zhi-Guang Yuan ◽  
Qiang Wang ◽  
Ang Zheng ◽  
Kai Zhang ◽  
Liang-Qiu Lu ◽  
...  
Keyword(s):  
Visible Light ◽  
Mild Conditions ◽  
Wide Range

We have developed an unprecedented route to carbazole by a visible light-photocatalysed formal (4+2) cycloaddition of indole-derived bromides and alkynes. Using this method, a wide range of highly functionalised carbazoles were produced in good yields under mild conditions.

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