A straightforward green synthesis of N-(tert-butylsulfinyl)imines

Abstract

A straightforward and environment-friendly protocol for the synthesis of valuable chiral N-(tert-butylsulfinyl)imines has been developed. Different from traditional process with benzaldehydes as substrates, arylmethyl alcohols, benzylthiol, dibenzyl ether, thioether, and disulfide are used as alternative substrates to react with tert-butanesulfinamide in the presence of KO^tBu under air for the synthesis of chiral N-(tert-butylsulfinyl)imines. This is a transition metal-free, mild, cost-effective, and simple process.

Keywords:

• N-(tert-butylsulfinyl)imines
• tert-butanesulfinamide
• aerobic oxidation
• green synthesis
• potassium tert-butoxide

Acknowledgments

We thank the National Natural Science Foundation of China (No. 21372034) and the cultivating program for excellent innovation team of Chengdu University of Technology (No. HY0084) for financial support. Dr Zhou thanks the grants from the Specialized Research Fund for the Doctoral Program of Higher Education (New Teachers) (No. 20135122120002).

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

National Natural Science Foundation of China [grant number 21372034]; Ministry of Science and Technology of the People's Republic of China [grant number 2013DFA21690]; Science & Technology Department of Sichuan Province [grant number 2016HH0074]; Chengdu University of Technology [grant number HY0084]; Specialized Research Fund for the Doctoral Program of Higher Education (New Teachers) [grant number 20135122120002].