Copper nitrate-catalyzed oxidative coupling of unactivated C(sp3)–H bonds of ethers and alkanes with N-hydroxyphthalimide: synthesis of N-hydroxyimide esters
Literature Information
Publication Date
2017-10-26
DOI
10.1039/C7OB02249B
Impact Factor
3.876
Authors
Xiaohe Xu, Jian Sun, Yuyan Lin, Jingya Cheng, Pingping Li, Yiyan Yan
View Original
Abstract
A copper nitrate-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) and ethers/alkanes has been described. The reaction is accomplished smoothly by using simple and green molecular oxygen as the oxidant, providing an alternative for the efficient synthesis of N-alkoxyphthalimides. In addition, it was found that when tert-butyl ethers were used as substrates, unexpected N-hydroxyimide ester derivatives were obtained in moderate to excellent yields. To further understand this unusual transformation, control experiments were performed and a plausible mechanism was proposed.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
N-Methyl-2-(4-nitrophenyl)ethanamine hydrochloride (1:1)
CAS Number:
166943-39-1
Molecular Formula:
C9H13ClN2O2
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