Highly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complex

Vanessa Kar Yan Lo; Zhen Guo; Matthew Kwok Wai Choi; Wing Yiu Yu; Jie Sheng Huang; Chi Ming Che

doi:10.1021/ja3006989

Highly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complex

Vanessa Kar Yan Lo, Zhen Guo, Matthew Kwok Wai Choi, Wing Yiu Yu, Jie Sheng Huang, Chi Ming Che

Research output: Journal article publication › Journal article › Academic research › peer-review

60 Citations (Scopus)

Abstract

Complex [(p-cymene)Ru(η1-O2CCF3)2(OH2)] mediated transformation of α-diazoacetamides ArCH2N(C(CH3)3)C(O)CHN2to result in carbene insertion into the primary C-H bond exclusively, with the γ-lactam products being isolated in up to 98% yield. This unexpected reaction is striking in view of the presence of usually more reactive sites such as secondary C-H bonds in the substrates. DFT calculations based on proposed Ru-carbene species provide insight into this unique selectivity.

Original language	English
Pages (from-to)	7588-7591
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	18
DOIs	https://doi.org/10.1021/ja3006989
Publication status	Published - 9 May 2012

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja3006989

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title = "Highly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complex",

abstract = "Complex [(p-cymene)Ru(η1-O2CCF3)2(OH2)] mediated transformation of α-diazoacetamides ArCH2N(C(CH3)3)C(O)CHN2to result in carbene insertion into the primary C-H bond exclusively, with the γ-lactam products being isolated in up to 98% yield. This unexpected reaction is striking in view of the presence of usually more reactive sites such as secondary C-H bonds in the substrates. DFT calculations based on proposed Ru-carbene species provide insight into this unique selectivity.",

author = "Lo, {Vanessa Kar Yan} and Zhen Guo and Choi, {Matthew Kwok Wai} and Yu, {Wing Yiu} and Huang, {Jie Sheng} and Che, {Chi Ming}",

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doi = "10.1021/ja3006989",

language = "English",

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journal = "Journal of the American Chemical Society",

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Highly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complex. / Lo, Vanessa Kar Yan; Guo, Zhen; Choi, Matthew Kwok Wai et al.
In: Journal of the American Chemical Society, Vol. 134, No. 18, 09.05.2012, p. 7588-7591.

Research output: Journal article publication › Journal article › Academic research › peer-review

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T1 - Highly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complex

AU - Lo, Vanessa Kar Yan

AU - Guo, Zhen

AU - Choi, Matthew Kwok Wai

AU - Yu, Wing Yiu

AU - Huang, Jie Sheng

AU - Che, Chi Ming

PY - 2012/5/9

Y1 - 2012/5/9

N2 - Complex [(p-cymene)Ru(η1-O2CCF3)2(OH2)] mediated transformation of α-diazoacetamides ArCH2N(C(CH3)3)C(O)CHN2to result in carbene insertion into the primary C-H bond exclusively, with the γ-lactam products being isolated in up to 98% yield. This unexpected reaction is striking in view of the presence of usually more reactive sites such as secondary C-H bonds in the substrates. DFT calculations based on proposed Ru-carbene species provide insight into this unique selectivity.

AB - Complex [(p-cymene)Ru(η1-O2CCF3)2(OH2)] mediated transformation of α-diazoacetamides ArCH2N(C(CH3)3)C(O)CHN2to result in carbene insertion into the primary C-H bond exclusively, with the γ-lactam products being isolated in up to 98% yield. This unexpected reaction is striking in view of the presence of usually more reactive sites such as secondary C-H bonds in the substrates. DFT calculations based on proposed Ru-carbene species provide insight into this unique selectivity.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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Highly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complex

Abstract

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