Details

Autor(en) / Beteiligte

• Cheng, Guolin
• Wang, Peng
• Yu, Jin‐Quan

Titel

meta‐C−H Arylation and Alkylation of Benzylsulfonamide Enabled by a Palladium(II)/Isoquinoline Catalyst

Ist Teil von

• Angewandte Chemie (International ed.), 2017-07, Vol.56 (28), p.8183-8186

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2017

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• Palladium(II)‐catalyzed meta‐C−H arylation and alkylation of benzylsulfonamide using 2‐carbomethoxynorbornene (NBE‐CO2Me) as a transient mediator are realized by using a newly developed electron‐deficient directing group and isoquinoline as a ligand. This protocol features broad substrate scope and excellent functional‐group tolerance. The meta‐substituted benyzlsulfonamides can be readily transformed into sodium sulfonates, sulfonate esters, and sulfonamides, as well as styrenes by Julia‐type olefination. The unique impact of the isoquinoline ligand underscores the importance of subtle matching between ligands and the directing groups. As directed: Palladium(II)‐catalyzed meta‐C−H arylation and alkylation of benzylsulfonamide, using 2‐carbomethoxynorbornene (NBE‐CO2Me) as a transient mediator, are realized using isoquinoline as a ligand. This protocol features broad substrate scope and excellent functional‐group tolerance. The meta‐substituted benzylsulfonamides can be readily transformed into sodium sulfonates, sulfonate esters, and sulfonamides, as well as styrenes by Julia‐type olefination.