Although alkynes are one of the smallest functional groups, they are among the most versatile building blocks for organic chemistry. In this feature article, the progress in alkynylation with hypervalent iodine reagents since 2018 will be presented.
Visible light triggers aromatization-driven C–C cleavage of dihydroquinazolinones to generate carbamoyl radicals, which are trapped by EBX reagents to furnish ynamides under photocatalyst-free conditions.
4CzIPN, a metal-free photocatalyst, enables sustainable synthesis with high photoluminescence, TADF, and long excited-state lifetime. It supports C–C/C–X bond formation, decarboxylation, acylation, and cyclization, often paired with metals.
A one-pot synthesis of bis(trifluoromethylated)benziodoxoles from iodine(I) precursors has been developed. This method tolerates multiple functional groups on both alkyne and aromatic backbone.
A late-stage diversification strategy for synthesizing ynamides has been developed.