Rhodium-catalyzed cascade C-H/C-C cleavage and cyclization reactions of 3-amide substituted indoles with diynes to construct cyclopenta[]carbazoles have been developed. A strategy amide worked as a novel traceless directing group along with C-C bond cleavage via Friedel-Crafts-retro reaction has been disclosed in this protocol. This method exhibits a broad substrate scope and tolerates various functional groups, furnishing the carbazole derivatives in good to high yields.
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http://dx.doi.org/10.1021/acs.orglett.9b03969 | DOI Listing |
Org Lett
December 2024
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
Chem Commun (Camb)
December 2022
Academician Workstation, Changsha Medical University, Changsha 410219, P. R. China.
A straightforward approach to synthesise isocoumarins Rh(III)-catalyzed C-H/C-C bond activation/annulation cascade of enaminones and iodonium ylides has been explored. The established protocol is characterized by an exceedingly simple reaction system, high regioselectivity and good functional group tolerance. Moreover, this strategy may provide a new route to cleavage of the C(sp)-C(O) bond of unstrained ketones.
View Article and Find Full Text PDFOrg Lett
August 2022
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.
A Rh-catalyzed weak chelation-guided C4-alkylation of indoles has been accomplished using cyclopropanols as an alkylating agent via the cascade C-H and C-C bond activation. The substrate scope, functional group tolerance, and late-stage mutation of drug molecules are the important practical features.
View Article and Find Full Text PDFJ Org Chem
October 2020
Department Engineering Research Centre of Molecular Medicine of Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Xiamen Marine and Gene Drugs, Key Laboratory of Precision Medicine and Molecular Diagnosis of Fujian Universities, School of Biomedical Sciences, Huaqiao University, Xiamen 361021, P. R. China.
A facile synthesis of various 3-(alkoxyalkyl)-1-indoles from pyrazolidinones, 2-acetylenic ketones, and alkyl alcohols C-H/C-C bond activation has been developed. The reaction proceeds smoothly under the proper reaction conditions, and preliminary mechanistic studies suggest that NaOAc is crucial for C-C bond activation. The advantages of the present method represent a redox-neutral process and exhibit excellent chemo and regioselectivity.
View Article and Find Full Text PDFOrg Lett
January 2020
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry , Nankai University, Tianjin 300071 , People's Republic of China.
Rhodium-catalyzed cascade C-H/C-C cleavage and cyclization reactions of 3-amide substituted indoles with diynes to construct cyclopenta[]carbazoles have been developed. A strategy amide worked as a novel traceless directing group along with C-C bond cleavage via Friedel-Crafts-retro reaction has been disclosed in this protocol. This method exhibits a broad substrate scope and tolerates various functional groups, furnishing the carbazole derivatives in good to high yields.
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