Rh(III)-Catalyzed C–H Activation/Intramolecular Cyclization: Access to N-Acyl-2,3-dihydro-1H-carbazol-4(9H)-ones from Cyclic 2-Diazo-1,3-diketones and N-Arylamides

[Image: see text] A Rh(III)-catalyzed C–H activation/cyclization cascade reaction is described. The reaction involves cyclic 2-diazo-1,3-diketones and N-arylamides, and it proceeds via an intermolecular C–C bond formation and subsequent intramolecular C–N bond formation. A variety of N-acyl-2,3-dihy...

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Autores principales: Zuo, Youpeng, He, Xinwei, Ning, Yi, Wu, Yuhao, Shang, Yongjia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645244/
https://www.ncbi.nlm.nih.gov/pubmed/31457387
http://dx.doi.org/10.1021/acsomega.7b01637
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author Zuo, Youpeng
He, Xinwei
Ning, Yi
Wu, Yuhao
Shang, Yongjia
author_facet Zuo, Youpeng
He, Xinwei
Ning, Yi
Wu, Yuhao
Shang, Yongjia
author_sort Zuo, Youpeng
collection PubMed
description [Image: see text] A Rh(III)-catalyzed C–H activation/cyclization cascade reaction is described. The reaction involves cyclic 2-diazo-1,3-diketones and N-arylamides, and it proceeds via an intermolecular C–C bond formation and subsequent intramolecular C–N bond formation. A variety of N-acyl-2,3-dihydro-1H-carbazol-4(9H)-ones were obtained under mild conditions in good to excellent yields (65–90%). Key features of this strategy include high-efficiency, operational simplicity, scalability, and broad functional-group tolerance. In addition, H(2)O and N(2) are the only byproducts. Carbazole derivatives with free NH groups can be easily obtained through N-deprotection reactions.
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spelling pubmed-66452442019-08-27 Rh(III)-Catalyzed C–H Activation/Intramolecular Cyclization: Access to N-Acyl-2,3-dihydro-1H-carbazol-4(9H)-ones from Cyclic 2-Diazo-1,3-diketones and N-Arylamides Zuo, Youpeng He, Xinwei Ning, Yi Wu, Yuhao Shang, Yongjia ACS Omega [Image: see text] A Rh(III)-catalyzed C–H activation/cyclization cascade reaction is described. The reaction involves cyclic 2-diazo-1,3-diketones and N-arylamides, and it proceeds via an intermolecular C–C bond formation and subsequent intramolecular C–N bond formation. A variety of N-acyl-2,3-dihydro-1H-carbazol-4(9H)-ones were obtained under mild conditions in good to excellent yields (65–90%). Key features of this strategy include high-efficiency, operational simplicity, scalability, and broad functional-group tolerance. In addition, H(2)O and N(2) are the only byproducts. Carbazole derivatives with free NH groups can be easily obtained through N-deprotection reactions. American Chemical Society 2017-11-30 /pmc/articles/PMC6645244/ /pubmed/31457387 http://dx.doi.org/10.1021/acsomega.7b01637 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Zuo, Youpeng
He, Xinwei
Ning, Yi
Wu, Yuhao
Shang, Yongjia
Rh(III)-Catalyzed C–H Activation/Intramolecular Cyclization: Access to N-Acyl-2,3-dihydro-1H-carbazol-4(9H)-ones from Cyclic 2-Diazo-1,3-diketones and N-Arylamides
title Rh(III)-Catalyzed C–H Activation/Intramolecular Cyclization: Access to N-Acyl-2,3-dihydro-1H-carbazol-4(9H)-ones from Cyclic 2-Diazo-1,3-diketones and N-Arylamides
title_full Rh(III)-Catalyzed C–H Activation/Intramolecular Cyclization: Access to N-Acyl-2,3-dihydro-1H-carbazol-4(9H)-ones from Cyclic 2-Diazo-1,3-diketones and N-Arylamides
title_fullStr Rh(III)-Catalyzed C–H Activation/Intramolecular Cyclization: Access to N-Acyl-2,3-dihydro-1H-carbazol-4(9H)-ones from Cyclic 2-Diazo-1,3-diketones and N-Arylamides
title_full_unstemmed Rh(III)-Catalyzed C–H Activation/Intramolecular Cyclization: Access to N-Acyl-2,3-dihydro-1H-carbazol-4(9H)-ones from Cyclic 2-Diazo-1,3-diketones and N-Arylamides
title_short Rh(III)-Catalyzed C–H Activation/Intramolecular Cyclization: Access to N-Acyl-2,3-dihydro-1H-carbazol-4(9H)-ones from Cyclic 2-Diazo-1,3-diketones and N-Arylamides
title_sort rh(iii)-catalyzed c–h activation/intramolecular cyclization: access to n-acyl-2,3-dihydro-1h-carbazol-4(9h)-ones from cyclic 2-diazo-1,3-diketones and n-arylamides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645244/
https://www.ncbi.nlm.nih.gov/pubmed/31457387
http://dx.doi.org/10.1021/acsomega.7b01637
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