A systematic investigation of ethynyl N-heterocycle-substituted-λ3-iodanes (ENHIs) is presented. In a straightforward one-pot synthesis these novel reagents can be obtained in high yields bearing variety N-heterocycles. Their reactivity as electrophilic alkyne group transfer was benchmarked well-established and inter- intramolecular reactions.

The relative (to BEt3) hydride ion affinity (HIA) of a series of acridine borenium salts has been calculated, with some HIAs found to be similar to that for [Ph3C]+. The HIA at the acridine C9 position is controlled by both acridine and the boron substituents, the latter presumably affecting the strength of the B=N bond in the acridane-BY2 products from hydride transfer. Through a range of hydr...