Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Metal-free Chlorothiolation of Alkenes using HCl and Sulfoxides.

Literature DB >> 30467455

Metal-free Chlorothiolation of Alkenes using HCl and Sulfoxides.

Abstract

We report a novel method for the chlorothiolation of alkenes using HCl and sulfoxides to achieve the 1,2-difunctionalization of unactivated alkenes. The combination of our new HCl reagent (HCl/DMPU) with sulfoxides forms a unique chlorothiolation system. Both terminal and internal alkenes are suitable substrates. This method works at gram scale and is applicable in further synthetic elaborations.

Entities: Chemical Disease Gene

Keywords: Alkene; Chlorothiolation; Difunctionalization; Regioselective; Sulfoxides

Year: 2018 PMID： 30467455 PMCID： PMC6242710 DOI： 10.1002/ejoc.201800973

Source DB: PubMed Journal: European J Org Chem ISSN： 1099-0690

33 in total

1. Primary amides. A general nitrogen source for catalytic asymmetric aminohydroxylation of olefins.

Authors: Z P Demko; M Bartsch; K B Sharpless
Journal: Org Lett Date: 2000-07-27 Impact factor: 6.005

Review 2. Cyclooxygenase (COX) inhibitors: a comparative QSAR study.

Authors: Rajni Garg; Alka Kurup; Suresh Babu Mekapati; Corwin Hansch
Journal: Chem Rev Date: 2003-03 Impact factor: 60.622

3. Data-mining for sulfur and fluorine: an evaluation of pharmaceuticals to reveal opportunities for drug design and discovery.

Authors: Elizabeth A Ilardi; Edon Vitaku; Jon T Njardarson
Journal: J Med Chem Date: 2013-10-29 Impact factor: 7.446

Metal-free Chlorothiolation of Alkenes using HCl and Sulfoxides.

1. Primary amides. A general nitrogen source for catalytic asymmetric aminohydroxylation of olefins.

Review 2. Cyclooxygenase (COX) inhibitors: a comparative QSAR study.

3. Data-mining for sulfur and fluorine: an evaluation of pharmaceuticals to reveal opportunities for drug design and discovery.

4. Regioselective Ene-Type Allylic Chlorination of Electron-Rich Alkenes by Activated DMSO.

5. Bromination of olefins with HBr and DMSO.

6. Catalytic, enantioselective, intramolecular carbosulfenylation of olefins. Preparative and stereochemical aspects.

7. Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of β-Keto Thioethers.

Review 8. Transfer of sulfur: from simple to diverse.

9. S-Michael additions to chiral dehydroalanines as an entry to glycosylated cysteines and a sulfa-Tn antigen mimic.

10. Chloride-Tolerant Gold(I)-Catalyzed Regioselective Hydrochlorination of Alkynes.

1. A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines.