Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 20, Pages 9818-9825Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo5011262
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Funding
- Shanghai Municipal Education Commission [14ZZ159]
- Shanghai Municipal Science and Technology Commission [12430501300]
- National Natural Science Foundation of China [21072032, 21272039]
- Special Scientific Foundation for Outstanding Young Teachers in Shanghai [ZZGJD13020]
- City Level Subjects of Shanghai University of Engineering and Technology [14XKCZ04]
- Program for Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Education
- Shanghai University of Engineering Science [E1-0501-14-0124, NHRC-2014-05]
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Microwave irradiation promoted the intramolecular cycloaddition of 2-azidoacetamides derived from a-chiral propargylic amines, affording 1,4,5-trisubstituted triazoles 4 bearing a chiral aminomethyl side chain at C5. In contrast, for the same substrates 3a-k, Cu(I)-NHC complexes catalyzed the intermolecular cycloaddition in an unexpected desilylative fashion, leading to 1,4-disubstituted triazoles 5. This demonstrates that 1-silyl alkynes can be employed as substrates for CuAAC with a suitable coupling partner.
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