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Org Biomol Chem. 2019 Jun 28;17(24):5891-5896. doi: 10.1039/c9ob00924h. Epub 2019 Jun 5.

One stone two birds: cobalt-catalyzed in situ generation of isocyanates and benzyl alcohols for the synthesis of N-aryl carbamates.

Author information

1
Key Laboratory of Chemistry in Ethnic Medicinal Resources, Yunnan Minzu University, Kunming 650500, China. FanBM@ynni.edu.cn.
2
Chongqing Academy of Chinese Materia Medica, Chongqing, 400065, China. neimen@163.com.

Abstract

An efficient method for the synthesis of N-aryl carbamates from N-Boc-protected amines has been developed. The cobalt-catalyzed in situ generation of isocyanates from N-Boc-protected amines and benzyl alcohols from benzyl formates has been achieved for the first time, which in turn furnished the corresponding benzyl carbamates in moderate to high yields. The reaction was catalyzed by CoI2 with tris-(4-dimethylaminophenyl)-phosphine as the ligand and zinc powder as the reductant. The developed reaction conditions were found to be compatible for aromatic amines with both electron-donating and -withdrawing substituents.

PMID:
31166354
DOI:
10.1039/c9ob00924h

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