Selective oxidation of unactivated C-H bonds by supramolecular control | Health & Environmental Research Online (HERO)

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HERO ID

2857279

Reference Type

Journal Article

Title

Selective oxidation of unactivated C-H bonds by supramolecular control

Author(s)

Fung, YS; Yan, SC; Wong, MK

Year

2012

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Journal

Organic and Biomolecular Chemistry
ISSN: 1477-0520
EISSN: 1477-0539

Volume

Issue

Page Numbers

3122-3130

Language

English

PMID

22411003

DOI

10.1039/c2ob07069c

Web of Science Id

WOS:000301958100030

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-84858993995&doi=10.1039%2fc2ob07069c&partnerID=40&md5=8461df001f9b305c84dada9379e22a9a
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Abstract

Efficient methods for dioxirane-based selective C-H bond oxidation by supramolecular control in H(2)O have been developed. With β-cyclodextrin as the supramolecular host, site-selective oxidation of the terminal over the internal tertiary C-H bond of 3,7-dimethyloctyl esters 3a-c was achieved. In addition, β-cyclodextrin selectively enhanced the C-H bond oxidation of cumene in a mixture of cumene and ethyl benzene in H(2)O. Through (1)H NMR studies, the selectivity in C-H bond oxidation could be attributed to the inclusion complex formation between β-cyclodextrin and the substrates.