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.

Visible-Light-Triggered Decarboxylative Alkylation of 8-Acylaminoquinoline with N-Hydroxyphthalimide Ester

Synlett ◽  
2020 ◽  
Vol 31 (07) ◽  
pp. 677-682 ◽  
Author(s):  
Bin Sun ◽  
Deyu Li ◽  
Xiaohui Zhuang ◽  
Rui Zhu ◽  
Aertuke Aisha ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Groups ◽  
Efficient Approach ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Operational Simplicity

A facile protocol for visible-light-induced decarboxylative radical coupling of NHP esters with 8-aminoquinoline amides is reported, affording a highly efficient approach to synthesize a variety of 2-alkylated or 2,4-dialkylated 8-aminoquinoline derivatives. The reaction proceeds smoothly without adding any ligand, and provides the corresponding products containing a wide range of functional groups in moderate to excellent yields. This reaction uses readily available starting materials, and proceeds under mild conditions and with operational simplicity.

Bromotrifluoromethane: A Useful Reagent for Hydrotrifluoromethylation of Alkenes and Alkynes

Synlett ◽  
2018 ◽  
Vol 29 (08) ◽  
pp. 1028-1032 ◽  
Author(s):  
Xing Zheng ◽  
Xingang Zhang ◽  
Yu-Yan Ren
Keyword(s):  
Visible Light ◽  
Organic Synthesis ◽  
Functional Group ◽  
Mild Conditions ◽  
Industrial Material ◽  
Reaction Proceeds

Bromotrifluoromethane (CF3Br) is a simple, inexpensive and abundant industrial material employed as a trifluoromethylating reagent. However, only limited strategies using CF3Br as a fluorine source are reported. Herein, we describe a visible-light-induced hydrotrifluoromethylation of alkenes and alkynes with CF3Br. The reaction proceeds under mild conditions with good functional group tolerance, providing a new route for the application of BrCF3 in organic synthesis.

Synthesis of Isoquinoline-1,3(2H,4H)-diones by Visible-light-mediated the Cyclization of Acryloylbenzamides with Alkyl Boronic Acids, Arylsulfonylhydrazides and Oxime Esters

Synthesis ◽  
2022 ◽  
Author(s):  
Jiahui Fu ◽  
Xingxing Cai ◽  
Yihuo Liu ◽  
Jing-Hua Li ◽  
Dongping Cheng ◽  
...  
Keyword(s):  
Visible Light ◽  
Bioactive Compounds ◽  
Boronic Acids ◽  
Radical Addition ◽  
Tandem Reaction ◽  
Good Opportunity ◽  
Mild Conditions ◽  
Reaction Proceeds

An efficient visible-light-mediated tandem reaction of acryloylbenzamides with alkyl boronic acids, arylsulfonylhydrazides and oxime esters is developed. The reaction proceeds the radical addition and cyclization to give various isoquinoline-1,3(2H,4H)-diones in satisfactory yields under mild conditions, which provides a good opportunity to discover new meaningful bioactive compounds.

scholarly journals Decarbonylation through Aldehydic C–H Bond Cleavage by a Cationic Iridium Catalyst

Synlett ◽  
2019 ◽  
Vol 30 (08) ◽  
pp. 972-976 ◽  
Author(s):  
Tomohiko Shirai ◽  
Kazuki Sugimoto ◽  
Masaya Iwasaki ◽  
Ryuki Sumida ◽  
Harunori Fujita ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Catalyst System ◽  
Mild Conditions ◽  
Iridium Catalyst ◽  
Reaction Proceeds ◽  
High Yields

We report the decarbonylation of aldehydes through an aldehydic C–H bond cleavage catalyzed by a cationic iridium/bisphosphine catalyst. The reaction proceeds under relatively mild conditions to give the corresponding hydrocarbon products in moderate to high yields. In addition, this cationic iridium catalyst system can be applied to an asymmetric hydroacylation of ketones.

A mild, general, and metal-free method for site-specific deuteration induced by visible light using D2O as the source of deuterium atoms

2020 ◽  
Vol 22 (3) ◽  
pp. 669-672 ◽  
Author(s):  
Shuai Shi ◽  
Ruining Li ◽  
Liangming Rao ◽  
Zhankui Sun
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Site Specific ◽  
Metal Free ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Radical Approach

Visible light induced desulfurization–deuteration method was developed using D2O as the source of deuterium atoms. This radical approach features mild conditions, broad substrate scope, highly efficient D-incorporation and excellent functional group compatibility.

Highly Enantioselective Michael Addition of Dithiomalonates to Nitroolefins Catalyzed by New Bifunctional Chiral Thioureas

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2577-2586 ◽  
Author(s):  
Jia-Ni Yuan ◽  
Hui-Xia Liu ◽  
Qin-Qin Tian ◽  
Nan Ji ◽  
Kuo Shen ◽  
...  
Keyword(s):  
Michael Addition ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Michael Adducts ◽  
Asymmetric Michael Addition ◽  
High Yields

We report a highly efficient asymmetric Michael addition of dithiomalonates to trans-β-nitroolefins catalyzed by versatile cinchona-based bifunctional thioureas, which provides the corresponding adducts in high yields (up to 92%) and with excellent enantioselectivities (up to 99% ee) under mild conditions. Replacement of the catalyst with its pseudo-enantiomer gives the Michael adducts with opposite configuration in similar yields and enantioselectivities.

A visible light mediated, metal and oxidant free highly efficient cross dehydrogenative coupling (CDC) reaction between quinoxalin-2(1H)-ones and ethers

2019 ◽  
Vol 43 (19) ◽  
pp. 7403-7408 ◽  
Author(s):  
Kishor D. Mane ◽  
Rohit B. Kamble ◽  
Gurunath Suryavanshi
Keyword(s):  
Visible Light ◽  
Transfer Process ◽  
White Light ◽  
Hydrogen Abstraction ◽  
Cyclic Ethers ◽  
Eosin Y ◽  
Highly Efficient ◽  
Dehydrogenative Coupling ◽  
Reaction Proceeds

The white light mediated, 3C alkylation of quinoxalin-2(1H)-ones via a cross dehydrogenative coupling (CDC) reaction with cyclic ethers using eosin Y as a photocatalyst is described. The reaction proceeds via a hydrogen abstraction and transfer process.

One-Pot Sequential Multistep Transformation of α,β-Unsaturated Trifluoromethyl Ketones: Facile Synthesis of Trifluoromethylated 2-Pyridones

Synlett ◽  
2019 ◽  
Vol 30 (05) ◽  
pp. 605-609 ◽  
Author(s):  
Fa-Guang Zhang ◽  
Jun-An Ma ◽  
Ning Lv ◽  
Yi-Qiang Tian
Keyword(s):  
Facile Synthesis ◽  
One Pot ◽  
Good Efficiency ◽  
Trifluoromethyl Ketones ◽  
Mild Conditions ◽  
Efficient Access ◽  
Reaction Proceeds ◽  
High Yields ◽  
Unsaturated Trifluoromethyl Ketones

A one-pot transformation of α,β-unsaturated trifluoromethyl ketones with 2-(phenylsulfinyl)acetamide to give trifluoromethylated 2-pyridones is realized. The reaction proceeds under mild conditions and involves multiple steps in an expeditious and controlled sequence to provide efficient access to a broad range of trifluoromethylated 2-pyridones in moderate to high yields. Moreover, further synthetic manipulations permit the routine synthesis of a diverse array of trifluoromethylated pyridines with good efficiency.

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.

Facile Synthesis of β-Keto Sulfones Employing Fenton’s Reagent in DMSO

Synlett ◽  
2018 ◽  
Vol 29 (05) ◽  
pp. 571-575 ◽  
Author(s):  
Vladimir Abaev ◽  
Olga Serdyuk ◽  
Petrakis Chalikidi ◽  
Maxim Uchuskin ◽  
Igor Trushkov
Keyword(s):  
Cost Effective ◽  
Fenton’S Reagent ◽  
Facile Synthesis ◽  
Fenton's Reagent ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
High Yields ◽  
Straightforward Approach

A new facile method for the synthesis of β-keto sulfones employing xanthates, DMSO, and Fenton’s reagent is described. The reaction proceeds under very mild conditions providing a cost-effective straightforward approach to various β-keto sulfones in high yields.

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