K. Inamoto, Hitomi Okawa, Shoko Kikkawa
Oct 28, 2014
Citations
0
Influential Citations
17
Citations
Journal
Tetrahedron
Abstract
Abstract Tetramethylammonium fluoride (TMAF) and some alkali metal alkoxides were found to be effective activators for deprotonative functionalization of heteroarenes. Onium amide bases, generated in situ from the combination of aminosilanes and a catalytic amount of TMAF or alkali metal alkoxides efficiently deprotonated C–H bonds of a series of heteroarenes in the presence of an electrophile such as ketones and aldehydes under mild conditions (room temperature). Addition products were obtained generally in good yields, thus providing a highly practical and efficient deprotonation method.