Switchable and Scalable Heteroarylation of Primary Amines with 2-Chlorobenzothiazoles under Transition-Metal-Free and Solvent-Free Conditions

Hua Cheng, Yan-Qiu Zhu, Peng-Fei Liu, Kai-Qiang Yang, Jin Yan, Wei Sang, Xiao-Sheng Tang, Rui Zhang* and Cheng Chen*

*Hubei University of Arts and Science, 296 Longzhong Road, Xiangyang 441053; Wuhan University of Technology, 122 Luoshi Road, Wuhan 430070, P. R. China, Email: rzhangccnu163.com, chengchenwhut.edu.cn

H. Cheng, Y.-Q. Zhu, P.-F. Liu, K.-Q. Yang, J. Yan, W. Sang, X.-S. Tang, R. Zhang, C. Chen, J. Org. Chem., 2021, 86, 10288-10302.

DOI: 10.1021/acs.joc.1c01019

---

see article for more reactions

Abstract

A transition-metal-free and scalable C-N coupling protocol achieves the synthesis of 2-aminobenzothiazoles from 2-chlorobenzothiazoles and primary amines under solvent-free conditions. Moreover, introducing an appropriate amount of NaH completely switched the selectivity from mono- toward di-heteroarylation.

see article for more examples

---

---

Key Words

benzothiazoles, green chemistry

---

ID: J42-Y2021