Copper-catalyzed aerobic decarboxylative coupling between cyclic α-amino acids and diverse C-H nucleophiles with low catalyst loading

Jing Guo; Ying Xie; Qiao-Lei Wu; Wen-Tian Zeng; Albert S C Chan; Jiang Weng; Gui Lu

doi:10.1039/c8ra02340a

Copper-catalyzed aerobic decarboxylative coupling between cyclic α-amino acids and diverse C-H nucleophiles with low catalyst loading

RSC Adv. 2018 May 1;8(29):16202-16206. doi: 10.1039/c8ra02340a. eCollection 2018 Apr 27.

Authors

Jing Guo¹, Ying Xie¹, Qiao-Lei Wu¹, Wen-Tian Zeng¹, Albert S C Chan¹, Jiang Weng¹, Gui Lu¹

Affiliation

¹ Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Sun Yat-sen University Guangzhou 510006 China lugui@mail.sysu.edu.cn wengj2@mail.sysu.edu.cn +86-20-3994-3048.

Abstract

An aerobic decarboxylative cross-coupling of α-amino acids with diverse C-H nucleophiles has been realized using Cu₂(OH)₂CO₃ (1 mol%) as the catalyst under air. This protocol enables highly efficient formation of various C(sp³)-C(sp³), C(sp³)-C(sp²) and C(sp³)-C(sp) bonds under simple conditions without the use of any ligand or extra oxidant, providing a practical approach to numerous nitrogen-containing compounds in good to excellent yields. The efficiency and practicability were also demonstrated by the gram-scale experiment and three-step synthesis of a Rad51 inhibitor.