Radical Reactions Initiated by Dimethylzinc

Abstract

Alkyl radicals were efficiently generated from ethers and alkanes via hydrogen abstraction by the action of dimethylzinc-air to undergo addition to imines. This methodology realized the introduction of oxygenated C1-C3 units to imines. Further studies revealed an interesting chemoselectivity : ether radicals generated by dimethylzinc favor the addition to imines whereas triethylborane facilitates the addition of ether radicals to aldehydes. Besides, dimethylzinc was found to promote some unusual reactions such as the reaction of THF at the β-position with aldehydes and three-component coupling reaction of arylamine and two THF molecules.