Copper-catalyzed redox-neutral C-H amination with amidoximes

Hui Chen; Shunsuke Chiba

doi:10.1039/c3ob41871e

Copper-catalyzed redox-neutral C-H amination with amidoximes

Hui Chen, Shunsuke Chiba^*

^*Corresponding author for this work

Nanyang Technological University

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

73 Citations (Scopus)

Abstract

CuI-catalyzed reactions of N-alkylamidoximes afforded dihydroimidazoles via sp³ C-H amination. On the other hand, the reactions of N-benzoylamidoximes resulted in sp² C-H amination to form quinazolinones. The reaction mechanisms could be characterized as a redox-neutral radical pathway including a Cu(i)-Cu(ii) redox catalytic cycle.

Original language	English
Pages (from-to)	42-46
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	1
DOIs	https://doi.org/10.1039/c3ob41871e
Publication status	Published - Jan 7 2014
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Copper-catalyzed redox-neutral C-H amination with amidoximes",

abstract = "CuI-catalyzed reactions of N-alkylamidoximes afforded dihydroimidazoles via sp3 C-H amination. On the other hand, the reactions of N-benzoylamidoximes resulted in sp2 C-H amination to form quinazolinones. The reaction mechanisms could be characterized as a redox-neutral radical pathway including a Cu(i)-Cu(ii) redox catalytic cycle.",

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AU - Chiba, Shunsuke

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N2 - CuI-catalyzed reactions of N-alkylamidoximes afforded dihydroimidazoles via sp3 C-H amination. On the other hand, the reactions of N-benzoylamidoximes resulted in sp2 C-H amination to form quinazolinones. The reaction mechanisms could be characterized as a redox-neutral radical pathway including a Cu(i)-Cu(ii) redox catalytic cycle.

AB - CuI-catalyzed reactions of N-alkylamidoximes afforded dihydroimidazoles via sp3 C-H amination. On the other hand, the reactions of N-benzoylamidoximes resulted in sp2 C-H amination to form quinazolinones. The reaction mechanisms could be characterized as a redox-neutral radical pathway including a Cu(i)-Cu(ii) redox catalytic cycle.

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Copper-catalyzed redox-neutral C-H amination with amidoximes

Abstract

ASJC Scopus Subject Areas

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