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. 2007 Feb 26;48(9):1637-1639.
doi: 10.1016/j.tetlet.2006.12.136.

A new palladium-mediated approach to 4-N-arylamino-1-butanols from peroxidic tetrahydrofuran and primary aromatic amines

Henry F Russell  1 , John B Bremner, Jennifer Bushelle-Edghill, Melissa R Lewis, Stacey R Thomas, Floyd Bates
Affiliations

A new palladium-mediated approach to 4-N-arylamino-1-butanols from peroxidic tetrahydrofuran and primary aromatic amines

Henry F Russell et al. Tetrahedron Lett. .

Abstract

Reaction of primary aromatic amines with peroxidic tetrahydrofuran (THF) in the presence of hydrogen and 10% palladium on carbon catalyst results in THF ring opening to give 4-N-arylamino-1-butanols in good yield. The reaction mechanism is believed to involve a free-radical sequence resulting in an imino alcohol subsequently reduced to product.

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Figures

Scheme 1
Scheme 1
THF ring opening to form 4-N-arylamino-1-butanols.
Scheme 2
Scheme 2
A plausible mechanism for Pd mediated THF ring opening.
See this image and copyright information in PMC

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