52374-25-1Relevant articles and documents
Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides
Gillaizeau-Simonian, Nicolas,Barde, Etienne,Guérinot, Amandine,Cossy, Janine
supporting information, p. 4004 - 4008 (2021/02/11)
A cobalt-catalyzed 1,4-aryl migration/disulfonylation cascade applied to α-bromo N-sulfonyl amides was developed. The reaction was highly chemoselective, allowing the preparation of α-aryl amides possessing a variety of functional groups. The method was used as the key step to synthesize an alkaloid, (±)-deoxyeseroline. Mechanistic investigations suggest a radical process.
Arylation and alkenylation of activated alkyl halides using sulfonamides
Greaney, Michael F.,Johnson, Stuart,Kovács, Ervin
supporting information, p. 3222 - 3224 (2020/03/23)
A variety of quaternary aryl amino acid derivatives can be synthesised using tandem SN2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C-N and C-Caryl bond under simple conditions with no requirement for organometallics or transition metal catalysts. The reaction is also successful for alkenyl sulfonamides, producing sterically congested quaternary alkene amino acid derivatives.
Metal-free synthesis of activated ynesulfonamides and tertiary enesulfonamides
Andna, Lucile,Miesch, Laurence
supporting information, p. 5688 - 5692 (2019/06/19)
An operationally simple synthesis of activated ynesulfonamides and enesulfonamides is described. Ynesulfonamides can be obtained through reaction of sulfonylamides with activated bromoalkynes and Triton B in a short time at room temperature. Likewise, terminal alkynes react with sulfonylamides to provide enesulfonamides. Z/E enesulfonamides can be transformed exclusively into E enesulfonamides.
