title: Microwave-assisted or Cu-NHC-catalyzed cycloaddition of azido-disubstituted alkynes: bifurcation of reaction pathways.
abstract: Microwave irradiation promoted the intramolecular cycloaddition of 2-azidoacetamides derived from α-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.
authors.affiliation: College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science , 333 Longteng Road, Shanghai 201620, China.
authors.forename: Yuyu
authors.initials: Y
authors.lastname: Xia
authors.forename: Ling-yan
authors.initials: LY
authors.lastname: Chen
authors.forename: Shang
authors.initials: S
authors.lastname: Lv
authors.forename: Zhihua
authors.initials: Z
authors.lastname: Sun
authors.forename: Bing
authors.initials: B
authors.lastname: Wang
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D008872:Microwaves; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000480:Alkynes; D000588:Amines; D001386:Azides; D014230:Triazoles; D003300:Copper; D010293:Pargyline