Selective benzylic C–H monooxygenation mediated by iodine oxides

10Citations
Citations of this article
15Readers
Mendeley users who have this article in their library.

Abstract

A method for the selective monooxdiation of secondary benzylic C–H bonds is described using an N-oxyl catalyst and a hypervalent iodine species as a terminal oxidant. Combinations of ammonium iodate and catalytic N-hydroxyphthalimide (NHPI) were shown to be effective in the selective oxidation of n-butylbenzene directly to 1-phenylbutyl acetate in high yield (86%). This method shows moderate substrate tolerance in the oxygenation of substrates containing secondary benzylic C–H bonds, yielding the corresponding benzylic acetates in good to moderate yield. Tertiary benzylic C–H bonds were shown to be unreactive under similar conditions, despite the weaker C–H bond. A preliminary mechanistic analysis suggests that this NHPI-iodate system is functioning by a radical-based mechanism where iodine generated in situ captures formed benzylic radicals. The benzylic iodide intermediate then solvolyzes to yield the product ester.

Cite

CITATION STYLE

APA

LaMartina, K. B., Kuck, H. K., Oglesbee, L. S., Al-Odaini, A., & Boaz, N. C. (2019). Selective benzylic C–H monooxygenation mediated by iodine oxides. Beilstein Journal of Organic Chemistry, 15, 602–609. https://doi.org/10.3762/bjoc.15.55

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free