Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides.
[reaction: see text] A general amination strategy for the N-alkynylation of carbamates, sulfonamides, and chiral oxazolidinones and imidazolidinones is described. A variety of substituted ynamides are available by deprotonation of amides with KHMDS followed by reaction with CuI and an alkynyl bromide.
Dunetz
Joshua R
JR
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Danheiser
Rick L
RL
D000480:Alkynes / Q000138:chemical synthesis*; D000577:Amides / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D013449:Sulfonamides / Q000737:chemistry*; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry
D000480:Alkynes; D000577:Amides; D002219:Carbamates; D013449:Sulfonamides; D003300:Copper; D014508:Urea