Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB(11)H(11)](−)

The preparation of the carborane acid chloride [1-(COCl)–CB(11)H(11)](−) from the carboxylic acid [1-(COOH)–CB(11)H(11)](−) is reported. This acid chloride exhibits remarkable inertness towards moisture and can be stored under ambient conditions for several months. Reaction with amines affords secon...

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Autores principales: Shen, Yunjun, Zheng, Kai, Dontha, Rakesh, Pan, Yani, Liu, Jiyong, Duttwyler, Simon
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9081092/
https://www.ncbi.nlm.nih.gov/pubmed/35539747
http://dx.doi.org/10.1039/c8ra03067g
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author Shen, Yunjun
Zheng, Kai
Dontha, Rakesh
Pan, Yani
Liu, Jiyong
Duttwyler, Simon
author_facet Shen, Yunjun
Zheng, Kai
Dontha, Rakesh
Pan, Yani
Liu, Jiyong
Duttwyler, Simon
author_sort Shen, Yunjun
collection PubMed
description The preparation of the carborane acid chloride [1-(COCl)–CB(11)H(11)](−) from the carboxylic acid [1-(COOH)–CB(11)H(11)](−) 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-(CONR(1)R(2))–CB(11)H(11)](−) 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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spelling pubmed-90810922022-05-09 Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB(11)H(11)](−) Shen, Yunjun Zheng, Kai Dontha, Rakesh Pan, Yani Liu, Jiyong Duttwyler, Simon RSC Adv Chemistry The preparation of the carborane acid chloride [1-(COCl)–CB(11)H(11)](−) from the carboxylic acid [1-(COOH)–CB(11)H(11)](−) 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-(CONR(1)R(2))–CB(11)H(11)](−) 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. The Royal Society of Chemistry 2018-06-19 /pmc/articles/PMC9081092/ /pubmed/35539747 http://dx.doi.org/10.1039/c8ra03067g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Shen, Yunjun
Zheng, Kai
Dontha, Rakesh
Pan, Yani
Liu, Jiyong
Duttwyler, Simon
Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB(11)H(11)](−)
title Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB(11)H(11)](−)
title_full Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB(11)H(11)](−)
title_fullStr Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB(11)H(11)](−)
title_full_unstemmed Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB(11)H(11)](−)
title_short Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB(11)H(11)](−)
title_sort efficient access to amides of the carborane carboxylic acid [1-(cooh)–cb(11)h(11)](−)
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9081092/
https://www.ncbi.nlm.nih.gov/pubmed/35539747
http://dx.doi.org/10.1039/c8ra03067g
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