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Literature DB >> 29424956

Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis.

Taehoon Kim¹, Stefan J McCarver², Chulbom Lee¹, David W C MacMillan².

Abstract

Herein we report a highly efficient method for nickel-catalyzed C-N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N-aryl and N-heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy-transfer mechanism wherein C-N bond reductive elimination occurs from a triplet excited NiII complex. Late-stage sulfonamidation in the synthesis of a pharmacologically relevant structure is also demonstrated.

Entities: Chemical Disease Gene

Keywords: energy transfer; heterocycles; nickel; photocatalysis; sulfonamides

Mesh：

Substances：

Year: 2018 PMID： 29424956 PMCID： PMC5937270 DOI： 10.1002/anie.201800699

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

21 in total

Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis.

1. Drug discovery: a historical perspective.

Review 2. Anticancer and antiviral sulfonamides.

3. Palladium-catalyzed intermolecular coupling of aryl halides and amides.

4. Photosensitized, energy transfer-mediated organometallic catalysis through electronically excited nickel(II).

5. Trap-Free Halogen Photoelimination from Mononuclear Ni(III) Complexes.

6. Aryl amination using ligand-free Ni(II) salts and photoredox catalysis.

Review 7. Carboxylic acid (bio)isosteres in drug design.

8. Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds.

9. Switching on elusive organometallic mechanisms with photoredox catalysis.

10. Photochemical Nickel-Catalyzed C-H Arylation: Synthetic Scope and Mechanistic Investigations.

1. Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides.

2. Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes.

3. Photochemically-Mediated, Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamate Esters.

4. Organometallic catalysis under visible light activation: benefits and preliminary rationales.

5. Bromine Radical Catalysis by Energy Transfer Photosensitization.

6. Energy Transfer to Ni-Amine Complexes in Dual Catalytic, Light-Driven C-N Cross-Coupling Reactions.

7. Developments in Photoredox/Nickel Dual-Catalyzed 1,2-Difunctionalizations.

8. N-Arylation of NH-Sulfoximines via Dual Nickel Photocatalysis.

9. Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols.

Review 10. Photosensitized direct C-H fluorination and trifluoromethylation in organic synthesis.