A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed. This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups.
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http://dx.doi.org/10.1021/ol4019634 | DOI Listing |
Org Lett
March 2024
School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei 230009, China.
A mild and effective strategy for the asymmetric synthesis of C2-quaternary indolin-3-ones from 2-alkynyl arylazides and ketones by gold/chiral amine relay catalysis is described. In this reaction, 2-alkynyl arylazides undergo gold-catalyzed cyclization, nucleophilic attack, and oxidation to form intermediate 2-phenyl-3-indol-3-ones, followed by an l-proline-catalyzed asymmetric Mannich reaction with ketones, to afford corresponding products in satisfactory yields with excellent enantio- and diastereoselectivities.
View Article and Find Full Text PDFJ Org Chem
August 2021
Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, People's Republic of China.
A novel and efficient synthetic method for the preparation of various pyrroloindolines from 2-alkynyl arylazides and thioacetamides was developed. The reaction was carried out in a one-pot process under mild reaction conditions to afford the products in moderate to good yields, which has the potential to be used in organic synthesis.
View Article and Find Full Text PDFOrg Biomol Chem
July 2017
Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.
An efficient method for the synthesis of 1H-indole-3-sulfonates via palladium-catalyzed tandem reactions of 2-alkynyl arylazides with sulfonic acids has been developed. The desired products were obtained in good to excellent yields under mild reaction conditions. The reactions were shown to proceed very fast, in most cases, within 10 min.
View Article and Find Full Text PDFJ Org Chem
January 2017
Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
A palladium-catalyzed synthesis of polysubstituted indoles and isoquinolines through the coupling of aryl bromides with 2-alkynyl arylazides or 2-alkynyl benzylazides has been developed. This method provides straightforward access to indoles and isoquinolines with high efficiency and excellent functional group compatibility. In this transformation, the iminophosphorane in situ generated from azides is served as the nucleophile that attacks the alkyne moiety in the cyclization process.
View Article and Find Full Text PDFOrg Lett
September 2016
Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
An unprecedented gold-catalyzed synthetic method for the direct assembly of aryl-annulated carbazoles from 2-alkynyl arylazides and alkynes is described. The reaction is proposed to proceed via a sequential cyclopropenation and intramolecular metal carbene/arene Friedel-Crafts-type reaction, respectively, mediated by two gold carbene intermediates.
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