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Regioselective Transfer Hydrodeuteration of Alkenes with a Hydrogen Deuteride Surrogate Using B(C6F5)3 Catalysis

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journal contribution
posted on 10.10.2018, 15:23 by Johannes C. L. Walker, Martin Oestreich
A regioselective hydrodeuteration of alkenes using monodeuterated cyclohexa-1,4-dienes as surrogates for hydrogen deuteride (HD) gas is reported. The metal-free process proceeds under B­(C6F5)3 catalysis presumably by deuteride abstraction to form borodeuteride [DB­(C6F5)3] and highly Brønsted-acidic Wheland intermediates. Low catalyst loadings (2.5 mol %) are used, and the reaction proceeds at room temperature.