N-Arylation of amines, amides, imides and sulfonamides with arylboroxines catalyzed by simple copper salt/EtOH system

• Zhang-Guo Zheng,
• Jun Wen,
• Na Wang,
• Bo Wu and
• Xiao-Qi Yu

Beilstein J. Org. Chem. 2008, 4, No. 40, doi:10.3762/bjoc.4.40

• , imides and sulfonamides catalyzed by a copper salt/EtOH system has been developed. In the absence of a base or additive the corresponding N-arylation products were obtained in moderate to excellent yields. Keywords: N-arylation; arylboroxine; copper salt; cross-coupling; ethanol; Introduction The

• anhydride form (boroxine) and not the free acid [21]. This result prompted us to study arylboroxines as aryl donors instead of arylboronic acids in the cross-coupling reaction, since arylboroxine is more active and may remarkably accelerate the reaction. In this paper we found that N-arylation reaction can

• be more efficiently promoted under milder reaction conditions when an arylboroxine was used. After the reaction conditions had been optimized, a more general and efficient catalytic system for the cross-coupling reaction of N-arylation was developed in presence of only simple copper salt (Scheme 1