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1.6.3.2 Reduction of Diols Using Rhenium Catalysts

DOI: 10.1055/sos-SD-226-00133

Tin, S.; de Vries, J. G.Science of Synthesis: Catalytic Reduction in Organic Synthesis, (20171236.

The deoxydehydration of diols to give alkenes using a primary or secondary alcohol as the reductant can be performed using catalysts based on various transition metals, such as vanadium and molybdenum;[‌37‌‌40‌] however, rhenium-based catalysts are by far the most commonly used.[‌34‌,‌41‌] In 2010, Bergman and co-workers described a process for the conversion of tetradecane-1,2-diol into tetradec-1-ene (9), using decacarbonyldirhenium(0) as the catalyst, in which the product is isolated in high yield (Scheme 10).[‌42‌] One of the advantages of this reaction is that it is performed under aerobic conditions. Octan-3-ol plays the role of the reductant, and is oxidized to the corresponding ketone during the process. Sulfuric acid can be used instead of 4-toluenesulfonic acid, but in that case an increase in the catalyst loading to 2.5 mol% is required to achieve the same levels of conversion and yield.

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References


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