Direct generation of oxygen-stabilized radicals by H• transfer from transition metal hydrides

Jonathan L. Kuo; John Hartung; Arthur Han; Jack R. Norton

doi:10.1021/ja511883b

Direct generation of oxygen-stabilized radicals by H• transfer from transition metal hydrides

Jonathan L. Kuo, John Hartung, Arthur Han, Jack R. Norton

Chemistry

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

60 Scopus citations

Abstract

Transition-metal hydrides generate α-alkoxy radicals by H• transfer to enol ethers. We have measured the rate constant for transfer from CpCr-(CO)₃H to n-butyl vinyl ether and have examined the chemistry of radicals generated by such transfers. Radicals from appropriate substrates undergo 5-exo cyclization, with higher diastereoselectivity than the analogous allcarbon radicals. From such radicals it is straightforward to make substituted tetrahydrofurans.

Original language	English (US)
Pages (from-to)	1036-1039
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	3
DOIs	https://doi.org/10.1021/ja511883b
State	Published - Jan 28 2015

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "Transition-metal hydrides generate α-alkoxy radicals by H• transfer to enol ethers. We have measured the rate constant for transfer from CpCr-(CO)3H to n-butyl vinyl ether and have examined the chemistry of radicals generated by such transfers. Radicals from appropriate substrates undergo 5-exo cyclization, with higher diastereoselectivity than the analogous allcarbon radicals. From such radicals it is straightforward to make substituted tetrahydrofurans.",

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AU - Han, Arthur

AU - Norton, Jack R.

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N2 - Transition-metal hydrides generate α-alkoxy radicals by H• transfer to enol ethers. We have measured the rate constant for transfer from CpCr-(CO)3H to n-butyl vinyl ether and have examined the chemistry of radicals generated by such transfers. Radicals from appropriate substrates undergo 5-exo cyclization, with higher diastereoselectivity than the analogous allcarbon radicals. From such radicals it is straightforward to make substituted tetrahydrofurans.

AB - Transition-metal hydrides generate α-alkoxy radicals by H• transfer to enol ethers. We have measured the rate constant for transfer from CpCr-(CO)3H to n-butyl vinyl ether and have examined the chemistry of radicals generated by such transfers. Radicals from appropriate substrates undergo 5-exo cyclization, with higher diastereoselectivity than the analogous allcarbon radicals. From such radicals it is straightforward to make substituted tetrahydrofurans.

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Direct generation of oxygen-stabilized radicals by H• transfer from transition metal hydrides

Abstract

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