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Literature DB >> 24692330

Gold-catalyzed intermolecular C-S bond formation: efficient synthesis of α-substituted vinyl sulfones.

Yumeng Xi¹, Boliang Dong, Edward J McClain, Qiaoyi Wang, Tesia L Gregg, Novruz G Akhmedov, Jeffrey L Petersen, Xiaodong Shi.

Abstract

A general method for the synthesis of α-substituted vinyl sulfones makes use of a combination of a triazole gold complex and gallium triflate. This efficient CS bond formation between simple terminal alkynes and sulfinic acids provides access to various α-substituted vinyl sulfones.

Entities: Chemical

Keywords: CS bond formation; Lewis acids; Markovnikov addition; gold; vinyl sulfones

Year: 2014 PMID： 24692330 DOI： 10.1002/anie.201310142

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

11 in total

1. A new cascade halosulfonylation of 1,7-enynes toward 3,4-dihydroquinolin-2(1H)-ones via sulfonyl radical-triggered addition/6-exo-dig cyclization.

Authors: Yi-Long Zhu; Bo Jiang; Wen-Juan Hao; Ai-Fang Wang; Jiang-Kai Qiu; Ping Wei; De-Cai Wang; Guigen Li; Shu-Jiang Tu
Journal: Chem Commun (Camb) Date: 2016-01-31 Impact factor: 6.222

Review 2. Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds.

Authors: Raju Jannapu Reddy; Arram Haritha Kumari
Journal: RSC Adv Date: 2021-03-01 Impact factor: 3.361

3. Synthesis and application of a novel bis-1,2,3-triazole ligand containing a 2,2'-bipyrrolidine core.

Authors: Stephen E Motika; Xiaodong Shi
Journal: ARKIVOC Date: 2018-01-28 Impact factor: 1.140

4. TBAI-assisted direct C-H activation of indoles with β-E-styrene sulfonyl hydrazides: a stereoselective access to 3-styryl thioindoles.

Authors: Saira Hafeez; Aamer Saeed
Journal: RSC Adv Date: 2021-04-27 Impact factor: 4.036

10. A mild light-induced cleavage of the S-O bond of aryl sulfonate esters enables efficient sulfonylation of vinylarenes.

Authors: Maxim Ratushnyy; Monika Kamenova; Vladimir Gevorgyan
Journal: Chem Sci Date: 2018-07-25 Impact factor: 9.825

Gold-catalyzed intermolecular C-S bond formation: efficient synthesis of α-substituted vinyl sulfones.

1. A new cascade halosulfonylation of 1,7-enynes toward 3,4-dihydroquinolin-2(1H)-ones via sulfonyl radical-triggered addition/6-exo-dig cyclization.

Review 2. Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds.

3. Synthesis and application of a novel bis-1,2,3-triazole ligand containing a 2,2'-bipyrrolidine core.

4. TBAI-assisted direct C-H activation of indoles with β-E-styrene sulfonyl hydrazides: a stereoselective access to 3-styryl thioindoles.

5. Transition-metal-free synthesis of 3-sulfenylated chromones via KIO₃-catalyzed radical C(sp²)-H sulfenylation.

Review 6. From CO₂ activation to catalytic reduction: a metal-free approach.

7. Anatomy of gold catalysts: facts and myths.

8. Oxidative β-C-H sulfonylation of cyclic amines.

9. The hydrogen atom transfer reactivity of sulfinic acids.

10. A mild light-induced cleavage of the S-O bond of aryl sulfonate esters enables efficient sulfonylation of vinylarenes.

Review 2. Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds.

Review 6. From CO2 activation to catalytic reduction: a metal-free approach.

Review 2. Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds.

Review 6. From CO₂ activation to catalytic reduction: a metal-free approach.