Use of tetramethylammonium fluoride (TMAF) and alkali metal alkoxides as an activator for catalytic deprotonative functionalization of heteroaromatic C(sp(2))-H bonds

作者：Inamoto Kiyofumi^*; Okawa Hitomi; Kikkawa Shoko; Kondo Yoshinori

来源：Tetrahedron, 2014, 70(43): 7917-7922.

DOI：10.1016/j.tet.2014.08.054

• Deprotonation
• Heteroarenes
• Tetramethylammonium fluoride
• Alkali metal alkoxides

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.

• 出版日期2014-10-28