期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 362, 期 2, 页码 417-423出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901472
关键词
C-H hydroxylation; oxidation; chemoselective; site-selective; late stage functionalization
资金
- NIH NIGMS Maximizing Investigator's Research Award MIRA [R35 GM122525]
- American Australian Association
Aromatic and heterocyclic functionality are ubiquitous in pharmaceuticals. Herein, we disclose a new Mn(PDP) catalyst system using chloroacetic acid additive capable of chemoselectively oxidizing remote tertiary C(sp(3))-H bonds in the presence of a broad range of aromatic and heterocyclic moieties. Although catalyst loadings can be lowered to 0.1 mol% under a Mn(PDP)/acetic acid system for aromatic and non-basic nitrogen heterocycle substrates, the Mn(PDP)/chloroacetic acid system generally affords 10-15% higher isolated yields on these substrates and is uniquely effective for remote C(sp(3))-H hydroxylations in substrates housing basic nitrogen heterocycles. The demonstrated ability to perform Mn(PDP)/chloroacetic acid C(sp(3))-H oxidations in pharmaceutically relevant complex molecules on multi-gram scales will facilitate drug discovery processes via late-stage functionalization.
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