School of Natural Sciences, University
of California, Merced, 5200 North Lake Road, Merced, California 95343, United States
of California, Merced, 5200 North Lake Road, Merced, California 95343, United States
J. Am. Chem. Soc., 2016, 138 (19), pp 6107–6110
DOI: 10.1021/jacs.6b02132
Publication Date (Web): May 02, 2016
Copyright © 2016 American Chemical Society
Abstract
There
are few examples of catalytic transfer hydrogenations of simple alkenes
and alkynes that use water as a stoichiometric H or D atom donor. We
have found that diboron reagents efficiently mediate the transfer of H
or D atoms from water directly onto unsaturated C–C bonds using a
palladium catalyst. This reaction is conducted on a broad variety of
alkenes and alkynes at ambient temperature, and boric acid is the sole
byproduct. Mechanistic experiments suggest that this reaction is made
possible by a hydrogen atom transfer from water that generates a
Pd–hydride intermediate. Importantly, complete deuterium incorporation
from stoichiometric D2O has also been achieved.
are few examples of catalytic transfer hydrogenations of simple alkenes
and alkynes that use water as a stoichiometric H or D atom donor. We
have found that diboron reagents efficiently mediate the transfer of H
or D atoms from water directly onto unsaturated C–C bonds using a
palladium catalyst. This reaction is conducted on a broad variety of
alkenes and alkynes at ambient temperature, and boric acid is the sole
byproduct. Mechanistic experiments suggest that this reaction is made
possible by a hydrogen atom transfer from water that generates a
Pd–hydride intermediate. Importantly, complete deuterium incorporation
from stoichiometric D2O has also been achieved.
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