Pd-PEPPSI-IPentAn Promoted Deactivated Amination of Aryl Chlorides with Amines under Aerobic Conditions

Fei-Dong Huang; Chang Xu; Dong-Dong Lu; Dong-Sheng Shen; Tian Li; Feng-Shou Liu

doi:10.1021/acs.joc.8b01205

Pd-PEPPSI-IPent^An Promoted Deactivated Amination of Aryl Chlorides with Amines under Aerobic Conditions

J Org Chem. 2018 Aug 17;83(16):9144-9155. doi: 10.1021/acs.joc.8b01205. Epub 2018 Jul 19.

Authors

Fei-Dong Huang¹, Chang Xu¹, Dong-Dong Lu¹, Dong-Sheng Shen¹, Tian Li¹, Feng-Shou Liu¹

Affiliation

¹ School of Chemistry and Chemical Engineering, Guangdong Cosmetics Engineering & Technology Research Center , Guangdong Pharmaceutical University , Zhongshan , Guangdong 528458 , China.

PMID: 29989415
DOI: 10.1021/acs.joc.8b01205

Abstract

We report herein a highly efficient Pd-catalyzed amination by "bulky-yet-flexible" Pd-PEPPSI-IPent^An complexes. The relationship between the N-heterocyclic carbenes (NHCs) structure and catalytic properties was discussed. Sterically hindered (hetero)aryl chlorides and a variety of aliphatic and aromatic amines can be applied in this cross-coupling, which smoothly proceeded to provide desired products. The operationally simple protocol highlights the rapid access to C_Ar-N bond formation under mild conditions without the exclusion of air and moisture.