Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB11H11]−

Yunjun Shen; Kai Zheng; Rakesh Dontha; Yani Pan; Jiyong Liu; Simon Duttwyler

doi:10.1039/C8RA03067G

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Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB₁₁H₁₁]⁻†

Yunjun Shen,‡^a Kai Zheng,‡^a Rakesh Dontha,^a Yani Pan,^a Jiyong Liu^a and Simon Duttwyler

*^a

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* Corresponding authors

^a Department of Chemistry, Zhejiang University, Zheda Road 38, 310027 Hangzhou, P.R. China
E-mail: duttwyler@zju.edu.cn

Abstract

The preparation of the carborane acid chloride [1-(COCl)–CB₁₁H₁₁]⁻ from the carboxylic acid [1-(COOH)–CB₁₁H₁₁]⁻ is reported. This acid chloride exhibits remarkable inertness towards moisture and can be stored under ambient conditions for several months. Reaction with amines affords secondary and tertiary carborane amides [1-(CONR¹R²)–CB₁₁H₁₁]⁻ in moderate to high yields under mild conditions. Two of the amide products were characterized by X-ray crystallography in addition to spectroscopic analysis. Preliminary studies show that the amides can be reduced to the corresponding amines and that the acid chloride has the potential to serve as a starting material for carborane ester formation.

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Article information

DOI: https://doi.org/10.1039/C8RA03067G
Article type: Paper
Submitted: 10 Apr 2018
Accepted: 11 Jun 2018
First published: 19 Jun 2018
This article is Open Access

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RSC Adv., 2018,8, 22447-22451

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Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB₁₁H₁₁]⁻

Y. Shen, K. Zheng, R. Dontha, Y. Pan, J. Liu and S. Duttwyler, RSC Adv., 2018, 8, 22447 DOI: 10.1039/C8RA03067G

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