Electrochemical, Iodine-Mediated α-CH Amination of Ketones by Umpolung of Silyl Enol Ethers
The electrochemical, oxidative Umpolung reaction of silyl enol ethers utilizing simple iodide salts for the synthesis of α-amino ketones is described. The products were isolated in excellent yields of up to 100percent, and various functionalized starting materials were accepted in an undivided electrochemical cell design. Moreover, a sensitivity assessment to ensure an improved reproducibility of the reaction and cyclic voltammetry experiments were performed to postulate a plausible reaction mechanism on their basis.
A convenient synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-4-ols by a novel intramolecular Barbier reaction and by an insertion reaction: Reaction scope and limitations
4-Substituted 1,2,3,4-tetrahydroisoquinolin-4-ols were prepared from N-(2-iodobenzyl)phenacylamines by an intramolecular Barbier reaction with butyllithium and by an insertion reaction with zerovalent nickel. The scope and limitations of these reactions were discussed.
A NEW INTRAMOLECULAR BARBIER REACTION OF N-(2-IODOBENZYL)PHENACYLAMINES: A CONVENIENT SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLIN-4-OLS
4-Phenyl-1,2,3,4-tetrahydroisoquinolin-4-ols were prepared by an intramolecular Barbier reaction of N-(2-iodobenzyl)phenacylamines with butyllithium in good yields.