Iodine-Catalyzed Synthesis of N,N'-Chelate Organoboron Aminoquinolate

Tianbao Yang; Xin Cao; Xing-Xing Zhang; Yifeng Ou; Chak-Tong Au; Shuang-Feng Yin; Renhua Qiu

doi:10.1021/acs.joc.0c01649

Iodine-Catalyzed Synthesis of N,N'-Chelate Organoboron Aminoquinolate

J Org Chem. 2020 Oct 2;85(19):12430-12443. doi: 10.1021/acs.joc.0c01649. Epub 2020 Sep 23.

Authors

Tianbao Yang¹, Xin Cao¹, Xing-Xing Zhang¹, Yifeng Ou¹, Chak-Tong Au², Shuang-Feng Yin¹, Renhua Qiu¹

Affiliations

¹ State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China.
² College of Chemistry and Chemical Engineering, Hunan Institute of Engineering, Xiangtan, 411104 Hunan, China.

PMID: 32929959
DOI: 10.1021/acs.joc.0c01649

Abstract

We disclose a novel method for the synthesis of fluorescent N,N'-chelate organoboron compounds in high efficiency by treatment of aminoquinolates with NaBAr₄/R'COOH in the presence of an iodine catalyst. These compounds display high air and thermal stability. A possible catalytic mechanism based on the results of control experiments has been proposed. Fluorescence quantum yield of 3b is up to 0.79 in dichloromethane.