Chemoselective Tertiary C−H Hydroxylation for Late‐Stage Functionalization with Mn(PDP)/Chloroacetic Acid Catalysis
2
Current address: Corteva Agriscience 9330 Zionsville Road Indianapolis, Indiana 46268
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Publication type: Journal Article
Publication date: 2019-12-26
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
PubMed ID:
32165875
General Chemistry
Abstract
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(sp3)-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(sp3)-H hydroxylations in substrates housing basic nitrogen heterocycles. The demonstrated ability to perform Mn(PDP)/chloroacetic acid C(sp3)-H oxidations in pharmaceutically relevant complex molecules on multi-gram scales will facilitate drug discovery processes via late-stage functionalization.
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Total citations:
30
Citations from 2024:
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(30%)
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GOST
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Chambers R. K. et al. Chemoselective Tertiary C−H Hydroxylation for Late‐Stage Functionalization with Mn(PDP)/Chloroacetic Acid Catalysis // Advanced Synthesis and Catalysis. 2019. Vol. 362. No. 2. pp. 417-423.
GOST all authors (up to 50)
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Chambers R. K., Zhao J., Delaney C. P., White M. Chemoselective Tertiary C−H Hydroxylation for Late‐Stage Functionalization with Mn(PDP)/Chloroacetic Acid Catalysis // Advanced Synthesis and Catalysis. 2019. Vol. 362. No. 2. pp. 417-423.
Cite this
RIS
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TY - JOUR
DO - 10.1002/adsc.201901472
UR - https://doi.org/10.1002/adsc.201901472
TI - Chemoselective Tertiary C−H Hydroxylation for Late‐Stage Functionalization with Mn(PDP)/Chloroacetic Acid Catalysis
T2 - Advanced Synthesis and Catalysis
AU - Chambers, Rachel K
AU - Zhao, Jinpeng
AU - Delaney, Connor P
AU - White, M.
PY - 2019
DA - 2019/12/26
PB - Wiley
SP - 417-423
IS - 2
VL - 362
PMID - 32165875
SN - 1615-4150
SN - 1615-4169
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Chambers,
author = {Rachel K Chambers and Jinpeng Zhao and Connor P Delaney and M. White},
title = {Chemoselective Tertiary C−H Hydroxylation for Late‐Stage Functionalization with Mn(PDP)/Chloroacetic Acid Catalysis},
journal = {Advanced Synthesis and Catalysis},
year = {2019},
volume = {362},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002/adsc.201901472},
number = {2},
pages = {417--423},
doi = {10.1002/adsc.201901472}
}
Cite this
MLA
Copy
Chambers, Rachel K., et al. “Chemoselective Tertiary C−H Hydroxylation for Late‐Stage Functionalization with Mn(PDP)/Chloroacetic Acid Catalysis.” Advanced Synthesis and Catalysis, vol. 362, no. 2, Dec. 2019, pp. 417-423. https://doi.org/10.1002/adsc.201901472.