TOWARDS DIRECT ALPHA-ARYLATION OF KETONES VIA OXIDATIVE UMPOLUNG OF ENOLATES

Modern state-of-the-art methodology allows exquisite flexibility arylation of enolates from halogenated arene starting materials.^1,2 However, direct arylation of ketones using simple arenes remains a challenging transformation.³ Recently we developed a method for the preparation of iodo(III)-enolates of ketones. Herein we report our studies towards developing the direct arylation and heteroarylation of ketone enolates via these iodo(III)-enolates culminating in our first successful results in this direction.

[1] Merritt, E. A.; Olofsson, B. Angew. Chem. Int. Ed. 2009, 48, 9052.

[2] Hypervalent iodine chemistry: Preparation, Structure and Synthetic Applications of Polyvalent Iodine compounds. First Edition. Viktor V. Zhdankin. © 2014 John Wiley & Sons Ltd.

[3] Singh, F.V.; Wirth T. Comprehensive Organic Synthesis II 2014, Vol. 7, 880.