Chemistry Commons^™

Propargyl Radicals In Organic Synthesis, Marcus Muresan, Hariharaputhiran Subramanian, Mukund P. Sibi, James R. Green

Chemistry and Biochemistry Publications

The appearance of propargyl radicals as synthetic intermediates has increased in recent years from a structural curiosity to a frequent occurrence. This minireview covers the synthetically relevant organic chemistry involving the intermediacy of propargyl radicals. The review is organized by the process employed in radical generation, including H-atom abstraction, propargyl-X homolyses, radical addition to enynes, reduction of polar C=X bonds, reductions of stable carbocations, and metal-mediated coupling reactions. The relevant mechanisms of generation and reaction are discussed, as are applications in syntheses of target molecules of interest.