University of Illinois

Jinpeng Zhao

M Christina White

Aaron L Petronico

Shauna M Paradine

Jennifer R Griffin

A chemoselective and reactive Mn(CF-PDP) catalyst system that enables for the first time the strategic advantages of late-stage aliphatic C&#x2014;H hydroxylation to be leveraged in aromatic compounds. This discovery will benefit small molecule therapeutics by enabling the rapid diversification of aromatic drugs and natural products and identification of their metabolites.

Chemoselective methylene hydroxylation in aromatic molecules

The invention provides novel manganese catalysts such as [Mn(BuPc)], which are general for the amination of all types of C(sp)-H bonds (aliphatic, allylic, propargylic, benzylic, ethereal), including strong 1aliphatic C&#x2014;H bonds, while achieving excellent chemoselectivity, stereospecificity, and high functional group tolerance. We demonstrate the late-stage diversification of bioactive complex molecules that encompass the range of C(sp)-H bond types, such as selective 1C&#x2014;H aminations of betulinic acid and pleuromutilin derivatives. The catalysts' unprecedented balance of reactivity and selectivity is in part attributed to its mechanism of C&#x2014;H amination that lies between stepwise and concerted.

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Indianapolis, IN, United States of America

Jinpeng Zhao