Details

Autor(en) / Beteiligte

• Chen, Mu-Yi
• Pannecoucke, Xavier
• Jubault, Philippe
• Besset, Tatiana

Titel

Pd-Catalyzed Selective Chlorination of Acrylamides at Room Temperature

Ist Teil von

• Organic letters, 2020-10, Vol.22 (19), p.7556-7561

Ort / Verlag

American Chemical Society

Erscheinungsjahr

2020

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• In this Letter, the transition-metal-catalyzed chlorination of alkenes is reported. In the presence of the commercially available and inexpensive N-chlorosuccinimide and without additive, the Pd-catalyzed chlorination of acrylamides by C–H bond activation was developed at room temperature under air. Under these mild reaction conditions, the versatility of the methodology was demonstrated as an array of acrylamides was functionalized to selectively provide the corresponding difficult-to-synthesize chlorinated olefins as a single Z stereoisomer. Mechanistic studies were conducted to get insights into the reaction mechanism, and post-functionalization reactions further demonstrated the synthetic utility of the approach toward the access to high value-added chlorinated compounds.