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Literature DB >> 14746462

Direct synthesis of sulfonamides and activated sulfonate esters from sulfonic acids.

Stephen Caddick¹, Jonathan D Wilden, Duncan B Judd.

Abstract

A general new method for the preparation of sulfonamides and activated sulfonate esters by the direct coupling of sulfonic acid salts with amines and alcohols using the reagent triphenylphosphine ditriflate is described. A new reusable polymer-supported reagent for these transformations under heterogeneous conditions is also described. These methods provide a fundamentally new approach to making small molecules containing the sulfonamide functional group.

Entities: Chemical

Mesh：

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Year: 2004 PMID： 14746462 DOI： 10.1021/ja0397658

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

16 in total

1. Synthesis and cross-coupling of sulfonamidomethyltrifluoroborates.

Authors: Gary A Molander; Nicolas Fleury-Brégeot; Marie-Aude Hiebel
Journal: Org Lett Date: 2011-03-02 Impact factor: 6.005

2. Synthesis of N-Substituted Sulfamate Esters from Sulfamic Acid Salts by Activation with Triphenylphosphine Ditriflate.

Authors: J Miles Blackburn; Melanie A Short; Thomas Castanheiro; Suraj K Ayer; Tobias D Muellers; Jennifer L Roizen
Journal: Org Lett Date: 2017-11-03 Impact factor: 6.005

3. Iodine-catalyzed sulfonylation of sulfonyl hydrazides with tert-amines: a green and efficient protocol for the synthesis of sulfonamides.

Authors: Jinyang Chen; Xiaoran Han; Lan Mei; Jinchuan Liu; Kui Du; Tuanwu Cao; Qiang Li
Journal: RSC Adv Date: 2019-10-02 Impact factor: 4.036

4. 3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: Aza-Michael addition reactions and the preparation of poly-HOPO chelators.

Authors: Gloria Martinez; Jayanthi Arumugam; Hollie K Jacobs; Aravamudan S Gopalan
Journal: Tetrahedron Lett Date: 2013-02-13 Impact factor: 2.415

5. Ph3P/CCl4 as a highly efficient reagent for one-pot N-alkylation of sulfonamides from alcohols: a rapid route to N-alkyl sulfonamides synthesis.

Authors: Mohammad Navid Soltani Rad; Somayeh Behrouz
Journal: Mol Divers Date: 2013-08-14 Impact factor: 2.943

10. Visible-Light, Iodine-Promoted Formation of N-Sulfonyl Imines and N-Alkylsulfonamides from Aldehydes and Hypervalent Iodine Reagents.

Authors: Megan D Hopkins; Zachary C Brandeburg; Andrew J Hanson; Angus A Lamar
Journal: Molecules Date: 2018-07-24 Impact factor: 4.411

Direct synthesis of sulfonamides and activated sulfonate esters from sulfonic acids.

1. Synthesis and cross-coupling of sulfonamidomethyltrifluoroborates.

2. Synthesis of N-Substituted Sulfamate Esters from Sulfamic Acid Salts by Activation with Triphenylphosphine Ditriflate.

3. Iodine-catalyzed sulfonylation of sulfonyl hydrazides with tert-amines: a green and efficient protocol for the synthesis of sulfonamides.

4. 3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: Aza-Michael addition reactions and the preparation of poly-HOPO chelators.

5. Ph3P/CCl4 as a highly efficient reagent for one-pot N-alkylation of sulfonamides from alcohols: a rapid route to N-alkyl sulfonamides synthesis.

6. Metal-Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO₂ , and Amines.

7. Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate.

8. Crystal structure of phenyl 2,4,5-tri-chloro-benzene-sulfonate.

9. Marine Sponge/CuO Nanocrystal: A Natural and Efficient Catalyst for Sulfonamides Synthesis.

10. Visible-Light, Iodine-Promoted Formation of N-Sulfonyl Imines and N-Alkylsulfonamides from Aldehydes and Hypervalent Iodine Reagents.