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36.7.1.1.4 Method 4: Pinacol Couplings

DOI: 10.1055/sos-SD-036-00589

Nativi, C.; Roelens, S.Science of Synthesis, (200836763.

The pinacol coupling reaction, although discovered in 1859,[‌38‌] is receiving renewed attention because of the more recent availability of mild and selective reducing agents.[‌39‌] The reaction involves the reductive homocoupling of a carbonyl compound to produce a symmetrically substituted 1,2-diol. The first step is a single-electron transfer of the carbonyl compound; this generates radical-ion intermediates that couple via CC bond formation to give a 1,2-diol (e.g., 14, Scheme 9). Highly substitued 1,2-diols tend to undergo dehydration with rearrangement (the pinacol rearrangement) under acid catalysis.

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