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Literature DB >> 15606121

Copper-catalyzed synthesis of vinyl sulfides.

Craig G Bates¹, Pranorm Saejueng, Michael Q Doherty, D Venkataraman.

Abstract

[reaction: see text] We report a method for the synthesis of vinyl sulfides using the soluble copper(I) catalyst [Cu(phen)(PPh3)2]NO3. The desired vinyl sulfides are obtained in good to excellent yields, with retention of stereochemistry. This protocol tolerates a wide variety of functional groups or substrates, is palladium-free, and does not require the use of expensive or air-sensitive additives.

Entities: Chemical Gene

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Year: 2004 PMID： 15606121 DOI： 10.1021/ol0477935

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

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Cited

12 in total

1. Base-mediated stereospecific synthesis of aryloxy and amino substituted ethyl acrylates.

Authors: M Shahjahan Kabir; Ojas A Namjoshi; Ranjit Verma; Michael Lorenz; V V N Phani Babu Tiruveedhula; Aaron Monte; Steven H Bertz; Alan W Schwabacher; James M Cook
Journal: J Org Chem Date: 2011-11-28 Impact factor: 4.354

2. Hydrothiolation of benzyl mercaptan to arylacetylene: application to the synthesis of (E) and (Z)-isomers of ON 01910·Na (Rigosertib®), a phase III clinical stage anti-cancer agent.

Authors: Venkat R Pallela; Muralidhar R Mallireddigari; Stephen C Cosenza; Balaiah Akula; D R C Venkata Subbaiah; E Premkumar Reddy; M V Ramana Reddy
Journal: Org Biomol Chem Date: 2013-02-06 Impact factor: 3.876

3. Resting state and elementary steps of the coupling of aryl halides with thiols catalyzed by alkylbisphosphine complexes of palladium.

Authors: Elsa Alvaro; John F Hartwig
Journal: J Am Chem Soc Date: 2009-06-10 Impact factor: 15.419

4. Unconventional Reactivity of Ethynylbenziodoxolone Reagents and Thiols: Scope and Mechanism.

Authors: Bin Liu; Juan V Alegre-Requena; Robert S Paton; Garret M Miyake
Journal: Chemistry Date: 2020-01-22 Impact factor: 5.236

5. Organophotoredox-Catalyzed Formation of Alkyl-Aryl and -Alkyl C-S/Se Bonds from Coupling of Redox-Active Esters with Thio/Selenosulfonates.

Authors: Yue Dong; Peng Ji; Yueteng Zhang; Changqing Wang; Xiang Meng; Wei Wang
Journal: Org Lett Date: 2020-12-10 Impact factor: 6.005

6. 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

Copper-catalyzed synthesis of vinyl sulfides.

1. Base-mediated stereospecific synthesis of aryloxy and amino substituted ethyl acrylates.

2. Hydrothiolation of benzyl mercaptan to arylacetylene: application to the synthesis of (E) and (Z)-isomers of ON 01910·Na (Rigosertib®), a phase III clinical stage anti-cancer agent.

3. Resting state and elementary steps of the coupling of aryl halides with thiols catalyzed by alkylbisphosphine complexes of palladium.

4. Unconventional Reactivity of Ethynylbenziodoxolone Reagents and Thiols: Scope and Mechanism.

5. Organophotoredox-Catalyzed Formation of Alkyl-Aryl and -Alkyl C-S/Se Bonds from Coupling of Redox-Active Esters with Thio/Selenosulfonates.

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

7. Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides.

8. Environmentally benign approach towards C-S cross-coupling reaction by organo-copper(II) complex.

9. Copper(II)-mediated O-arylation of protected serines and threonines.

10. Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions.