Hydrodebromination of Allylic Bromides with Water Catalyzed by Rhodium Porphyrin Complexes
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AbstractFor the reductive hydrodebromination, the reductants are usually H2 gas, alcohols, hydrosilanes, metal hydrides,
Grignard reagents and so on. Water, as a green, economically more attractive reducing agent, is generally believed
unlikely to be the hydrogen atom donor to carbon-centered radicals due to the high bond dissociation energy of the HOH bond (118 kcal/mol). Weakening this H-OH bond by the coordination of H2O to a Lewis acid makes H2O as a hydrogen atom donor possible. Successful examples employed Cp2TiIIICl, BMe3 or SmI2 as the Lewis acid.1 However, it involves a stoichiometric amount of the Lewis acid. Most recently, hydrogenation of alkenes and alkynes using water as a stoichiometric hydrogen atom donor was achieved by employing tetrahydroxydiboron as a sacrificial reductant. 2 As far as we are concerned, catalytic hydrodebromination using water as the hydrogen source without any other reductant remains unreported. Herein, based on our earlier success of employing water as the hydrogen source for hydrogenating carbon-carbon σ-bonds,3 we disclose a rhodium porphyrin complex catalyzed hydrodebromination of allylic bromides with water as the attractive hydrogen source without any sacrificial reductant.
Acceptance Date26/09/2016
All Author(s) ListYANG W, ZHANG H, CHAN K
Name of ConferenceThe 6th Junior International Conference on Cutting-Edge Organic Chemistry in Asia
Start Date of Conference24/10/2016
End Date of Conference26/10/2016
Place of ConferenceFukuoka
Country/Region of ConferenceJapan
Year2016
LanguagesEnglish-United States

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