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Literature DB >> 24499437

Silver-mediated radical aryltrifluoromethylthiolaton of activated alkenes.

Abstract

The first example of silver-mediated oxidative aryltrifluoromethylthiolation of activated alkenes to produce valuable trifluoromethylthiole-containing oxindoles was developed. Mechanistic investigations indicated that this novel transformation proceeded through a unique F3CS(•) radical addition path, thus providing a practical and easy-handling method to generate a F3CS(•) radical in the laboratory.

Entities: Chemical

Year: 2014 PMID： 24499437 DOI： 10.1021/ol403739w

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

5 in total

1. Direct phosphorylation of benzylic C-H bonds under transition metal-free conditions forming sp³C-P bonds.

Authors: Qiang Li; Chang-Qiu Zhao; Tieqiao Chen; Li-Biao Han
Journal: RSC Adv Date: 2022-06-24 Impact factor: 4.036

2. Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

Authors: Yong Li; Zhishi Ye; Tabitha M Bellman; Teng Chi; Mingji Dai
Journal: Org Lett Date: 2015-04-17 Impact factor: 6.072

Silver-mediated radical aryltrifluoromethylthiolaton of activated alkenes.

1. Direct phosphorylation of benzylic C-H bonds under transition metal-free conditions forming sp³C-P bonds.

2. Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

3. Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes.

4. Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles.

5. Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes.

Silver-mediated radical aryltrifluoromethylthiolaton of activated alkenes.

1. Direct phosphorylation of benzylic C-H bonds under transition metal-free conditions forming sp3C-P bonds.

2. Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

3. Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes.

4. Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles.

5. Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes.

1. Direct phosphorylation of benzylic C-H bonds under transition metal-free conditions forming sp³C-P bonds.