Photo-Induced N-N Coupling of o-Nitrobenzyl Alcohols and Indolines To Give N-Aryl-1-amino Indoles

Yifeng Ou; Tianbao Yang; Niu Tang; Shuang-Feng Yin; Nobuaki Kambe; Renhua Qiu

doi:10.1021/acs.orglett.1c02227

Photo-Induced N-N Coupling of o-Nitrobenzyl Alcohols and Indolines To Give N-Aryl-1-amino Indoles

Org Lett. 2021 Aug 20;23(16):6417-6422. doi: 10.1021/acs.orglett.1c02227. Epub 2021 Aug 6.

Authors

Yifeng Ou¹, Tianbao Yang¹, Niu Tang¹, Shuang-Feng Yin¹, Nobuaki Kambe^{1

2}, 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, People's Republic of China.
² The Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan.

PMID: 34355914
DOI: 10.1021/acs.orglett.1c02227

Abstract

A novel method to synthesize N-aryl-1-amino indoles was established by the photoinduced N-N coupling reaction. This protocol is by treatment of o-nitrobenzyl alcohols and indolines in the presence of TEAI and acetic acid with a 24 W ultraviolet (UV) light-emitting diode (LED) (385-405 nm) irradiation. The products bearing an aldehyde group can be further transformed to fluorescent probes based on Rhodamine 6G derivative 11, which shows a high specificity and sensitivity for Fe³⁺.

Publication types

Research Support, Non-U.S. Gov't