Zn(OTf)2-catalyzed addition of amines to carbodiimides: efficient synthesis of guanidines and unpredicted formation of Zn–N amido species

Dongzhen Li; Jie Guang; Wen-Xiong Zhang; Yang Wang; Zhenfeng Xi

doi:10.1039/B923249B

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Zn(OTf)₂-catalyzed addition of amines to carbodiimides: efficient synthesis of guanidines and unpredicted formation of Zn–N amido species†

Dongzhen Li,^a Jie Guang,^a Wen-Xiong Zhang,*^ab Yang Wang^a and Zhenfeng Xi*^a

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* Corresponding authors

^a Beijing National Laboratory for Molecular Sciences (BNLMS), and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China

^b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, China
E-mail: wx_zhang@pku.edu.cn, zfxi@pku.edu.cn
Fax: +86 10 62751708
Tel: +86 10 62758294

Abstract

Zn(OTf)₂ acts as an excellent catalyst precursor for addition of various amine N–H bonds to carbodiimides under an atmosphere of air, offering a convenient synthesis of substituted guanidines with high functional-group tolerance. A Zn–N amido species is shown to act as the active species.

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Article information

DOI: https://doi.org/10.1039/B923249B
Article type: Paper
Submitted: 05 Nov 2009
Accepted: 21 Jan 2010
First published: 08 Feb 2010

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Org. Biomol. Chem., 2010,8, 1816-1820

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Zn(OTf)₂-catalyzed addition of amines to carbodiimides: efficient synthesis of guanidines and unpredicted formation of Zn–N amido species

D. Li, J. Guang, W. Zhang, Y. Wang and Z. Xi, Org. Biomol. Chem., 2010, 8, 1816 DOI: 10.1039/B923249B

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Organic & Biomolecular Chemistry