Abstract
Copper acetylides are readily available and especially convenient reagents for the alkynylation of a broad range of heteronucleophiles. Upon simple activation with molecular oxygen in the presence of suitable ligands and solvents, they readily transfer their alkyne moiety at room temperature, notably yielding a variety of nitrogen- and phosphorus-substituted alkynes. We report in this manuscript an extensive study of the chemoselectivity of this alkynylation based on quantitative 13C NMR analyses. With suitable ligand/solvent combinations, various phosphorus-based nucleophiles can be alkynylated with excellent levels of selectivity, even in the presence of a large excess of a nitrogen-nucleophile. This chemoselective alkynylation could be further extended to an even more challenging selective alkynylation of a nitrogen-nucleophile over another one, further highlighting the synthetic potential of copper acetylides as alkynylating agents that can selectively “fish” a nucleophile without affecting others.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
