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Magnesium- and titanium-induced reductive coupling of carbonyl compounds: efficient syntheses of pinacols and alkenes

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Fürstner, A., Csuk, R., Rohrer, C., & Weidmann, H. (1988). Magnesium- and titanium-induced reductive coupling of carbonyl compounds: efficient syntheses of pinacols and alkenes. Journal of the Chemical Society, Perkin Transactions 1, (7), 1729-1734. doi:10.1039/P19880001729.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0010-2578-2
Abstract
Finely dispersed magnesium on graphite was found to be a totally selective single-electron transfer reagent of general utility for the redn. of various kinds of carbonyl and dicarbonyl compds. to pinacols, a reaction quite compatible with a no. of functional groups. Similarly, titanium on graphite proved to be a universally applicable reducing agent for the efficient conversion of pinacols, carbonyl and dicarbonyl compds. into alkenes and cycloalkenes resp. and for the cyclization of oxo alkanoates to enol ethers, facilitating and unifying the highly useful McMurry reaction. The practicability of the presently known carbonyl coupling methods is discussed in the light of these results.