Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules

Jennifer M. Howell; Kaibo Feng; Joseph R. Clark; Louis J. Trzepkowski; M. Christina White

doi:10.1021/jacs.5b10299

Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules

Jennifer M. Howell, Kaibo Feng, Joseph R. Clark, Louis J. Trzepkowski, M. Christina White

Research output: Contribution to journal › Article › peer-review

Abstract

Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Brønsted acid (HBF₄) or an azaphilic Lewis acid (BF₃) to enable remote, non-directed C(sp³)-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.

Original language	English (US)
Pages (from-to)	14590-14593
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	46
DOIs	https://doi.org/10.1021/jacs.5b10299
State	Published - Nov 25 2015

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.5b10299

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abstract = "Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Br{\o}nsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp3)-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.",

author = "Howell, {Jennifer M.} and Kaibo Feng and Clark, {Joseph R.} and Trzepkowski, {Louis J.} and White, {M. Christina}",

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AU - Howell, Jennifer M.

AU - Feng, Kaibo

AU - Clark, Joseph R.

AU - Trzepkowski, Louis J.

AU - White, M. Christina

PY - 2015/11/25

Y1 - 2015/11/25

N2 - Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Brønsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp3)-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.

AB - Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Brønsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp3)-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 46

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Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules

Abstract

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