Direct visible-light-mediated aminofluorination of styrenes has been developed with high regioselectivity. Shelf-stable N-Ts-protected 1-aminopyridine salt was used as the nitrogen-radical precursor, and the commercially available hydrogen fluoride-pyridine was used as the nucleophilic fluoride source. The synthesis of an analogue of LY503430 was performed to demonstrate the synthetic value of this strategy.
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http://dx.doi.org/10.1021/acs.orglett.8b01760 | DOI Listing |
J Org Chem
December 2021
Department of Chemistry, Renmin University of China, Beijing 100872, China.
The development of methods for the assembly of 1,2,3-triazoles is an important topic due to the broad applications of this motif in various scientific fields. In this work, we demonstrate that the three-component assembly of α-CF carbonyls, NaN, and amines was achieved for the selective construction of a variety of 5-amino -1,2,3-triazoles under transition-metal-free and open-air conditions. The method provides a general and operationally simple route to functionalized biologically important molecules including carbohydrates, nucleosides, and peptides and exhibits broad substrate scopes.
View Article and Find Full Text PDFOrg Lett
February 2021
Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Frontiers Science Center for Synthetic Biology (Ministry of Education), and Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, P. R. of China.
The unified construction of cyano-substituted 1,2,4-triazoles, particularly the 5-cyano counterparts, remains underdeveloped. Herein we describe a three-component method to access a wide range of 1-aryl 5-cyano-1,2,4-triazoles using readily available 2-diazoacetonitriles, nitriles, and aryldiazonium salts. This regiospecific synthesis relies on the dipolar [3 + 2] annulation of the formed nitrile ylides with aryldiazonium salts.
View Article and Find Full Text PDFEnviron Microbiol
February 2021
State Key Laboratory of Microbial Metabolism, Joint International Research Laboratory of Metabolic and Developmental Sciences, and School of Life Sciences and Biotechnology, Shanghai Jiao Tong University, Shanghai, 200240, China.
The chemical synthesis intermediate 3,4-dichloronitrobenzene (3,4-DCNB) is an environmental pollutant. Diaphorobacter sp. strain JS3050 utilizes 3,4-DCNB as a sole source of carbon, nitrogen and energy.
View Article and Find Full Text PDFOrg Lett
August 2018
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering , Lanzhou University, Lanzhou 730000 , P. R. China.
Direct visible-light-mediated aminofluorination of styrenes has been developed with high regioselectivity. Shelf-stable N-Ts-protected 1-aminopyridine salt was used as the nitrogen-radical precursor, and the commercially available hydrogen fluoride-pyridine was used as the nucleophilic fluoride source. The synthesis of an analogue of LY503430 was performed to demonstrate the synthetic value of this strategy.
View Article and Find Full Text PDFOrg Biomol Chem
May 2018
Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020, Antwerp, Belgium.
A zinc(ii) triflate catalyzed three component synthesis of 1,6-dihydropyridines, involving aldimines, alkynes and electron-deficient dimethyl acetylenedicarboxylate (DMAD), in good to excellent yields has been described. Besides a range of different N-substituents, a variety of both aromatic and aliphatic alkynes could be used. The application of electron-deficient propiolates instead of DMAD resulted in regiospecific incorporation of the ester functionality on the 1,6-dihydropyridine ring.
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