N-Heterocyclic carbenes are shown to cleanly abstract dihydrogen from organotin di- and trihydrides to intermediately form the reactive stannylene species [R2Sn] and [R′SnH], respectively, which undergo further reactions.

Although hydrides of the group 14 elements are well-known as versatile starting materials in many chemical transformations, a hydride of lead in oxidation state II is so far unknown. In this work, we finally complete the jigsaw puzzle by reporting the isolation of the first low valent organolead hydride. The thermolabile dimeric organolead hydride was synthesized at low temperature and features a hydride H NMR signal (in solution 35.61 ppm; in the solid state 31.1 ppm) at the lowest field observed so far for a diamagnetic compound in agreement with quantum chemical predictions.

Amine bases are shown to induce reductive elimination of dihydrogen from terphenyltin trihydride.

An efficient transition-metal-free amination of benzoxazoles has been developed. With catalytic amounts of tetrabutylammoniumiodide (TBAI), aqueous solutions of H(2)O(2) or TBHP as co-oxidant and under mild reaction conditions, highly desirable 2-aminobenzoxazoles were isolated in excellent yields of up to 93%. First mechanistic experiments indicate the in situ iodination of the secondary amine as the putative mode of activation.