Simple and Facile Benzylic C-H Oxidation Using (Diacetoxyiodo)benzene and Catalytic Sodium Azide

Abstract

A synthetic utility of hypervalent iodine reagent, (diacetoxyiodo)benzene, with a catalytic amount of sodium azide for oxidation of benzylic C-H to corresponding ketone compounds is described. The advantage of this protocol is characterized by mild reaction conditions and shorter reaction time to obtain moderate to good yields.

GRAPHICAL ABSTRACT

Keywords:

• Benzylic C-H
• (diacetoxyiodo)benzene
• ketones
• oxidation

ACKNOWLEDGMENT

K. A. S. thanks the Council of Scientific and Industrial Research (CSIR, New Delhi) for providing a junior research fellowship.

Notes

^a Reaction conditions: substrate (5.91 mmol), (diacetoxyiodo)benzene (2 equiv), and NaN₃ (0.1 equiv) in CH₃CN/H₂O (10 mL).

^b Isolated yields after column chromatography and structures were confirmed by comparison of IR and ¹H NMR with authentic materials.

^c No reaction.