Aminocatalytic Cross-Coupling Approach via Iminium Ions to Different C-C Bonds

作者：Mupparapu Nagaraju; Battini Narsaiah; Battula Satyanarayana; Khan Shahnawaz; Vishwakarma Ram A^*; Ahmed Qazi Naveed

来源：Chemistry - A European Journal, 2015, 21(7): 2954-2960.

DOI：10.1002/chem.201405477

• cross-coupling
• iminium cations
• organocatalysis
• oxidation
• synthetic methods

Given the attractive ability of iminium ions to functionalize molecules directly at ostensibly unreactive positions, the reactivity of iminium ions, in which an alpha CH2 group is replaced by C=O was explored. Background studies on the ability of such iminium cations to promote reactions via an iminium-catalyzed or iminium-equivalent pathway are apparently unavailable. Previously, tandem cross-coupling reactions were reported, in which an iminium ion undergoes nucleophilic 1,2-addition to give a putative three-component intermediate that abstracts a proton in situ and undergoes self-deamination followed by unprecedented DMSO/aerobic oxidation to generate alpha-ketoamides. However, later it was observed that iminium ions can generate valuable alpha-ketoamides through simple aerobic oxidation. In all reactions, iminium ions were generated in situ by reaction of 2-oxoaldehydes with secondary amines.

• 出版日期2015-2-9