A pinacol coupling reaction is an organic reaction in which a carbon–carbon bond is formed between the carbonyl groups of an aldehyde or a ketone in presence of an electron donor in a free radical process.[1] The reaction product is a vicinal diol. The reaction is named after pinacol (also known as 2,3-dimethyl-2,3-butanediol or tetramethylethylene glycol), which is the product of this reaction when done with acetone as reagent. The reaction is usually a homocoupling but intramolecular cross-coupling reactions are also possible. Pinacol was discovered by Wilhelm Rudolph Fittig in 1859.
^Fittig R (1859). "Ueber einige Producte der trockenen Destillation essigsaurer Salze" [On some products of the dry distillation of acetate salts]. Justus Liebigs Annalen der Chemie (in German). 110: 23–45. doi:10.1002/jlac.18591100103.
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A pinacolcouplingreaction is an organic reaction in which a carbon–carbon bond is formed between the carbonyl groups of an aldehyde or a ketone in presence...
organic chemistry, a couplingreaction is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid...
This reaction is related to the Pinacolcouplingreaction which also proceeds by reductive coupling of carbonyl compounds. This reductive coupling can...
be produced by the pinacol couplingreaction from acetone: As a vicinal-diol, it can rearrange to pinacolone by the pinacol rearrangement, e.g. by heating...
1835 – 19 November 1910) was a German chemist. He discovered the pinacolcouplingreaction, mesitylene, diacetyl and biphenyl. Fittig studied the action...
ring C. Two key chemical transformations are the Shapiro reaction and the pinacolcouplingreaction. The overall synthesis was published in 1995 in a series...
are also invoked as intermediates in the pinacolcouplingreaction. The ketyl radicals derived from the reaction of sodium and benzophenone is a common...
spectrum. This signal shows the characteristic coupling to any protons on the α carbon with a small coupling constant typically less than 3.0 Hz. The 13C...
routes to vic-diols are the hydrogenation of acyloins and the pinacolcouplingreaction. 1,3-Diols are often prepared industrially by aldol condensation...
tin tetrachloride reaction at room temperature. The Prins-pinacolreaction is a cascade reaction of a Prins reaction and a pinacol rearrangement. The...
Temperature-Stable Electride as a Synthetic Organic Reagent: Application to PinacolCouplingReaction in Aqueous Media". Org. Lett. 9 (21): 4287–4289. doi:10.1021/ol701885p...
Rudolph Fittig (1835–1910), German chemist. He discovered the pinacolcouplingreaction. Wilhelm Kühne (1837–1900), German physiologist. He coined the...
carbon is a pinacol rearrangement. While this reaction refers specifically to a vicinal dihydroxide rearrangement, there are other pinacol type rearrangements...
(February 2000). "1-Alkenylboronic acid pinacol esters can be synthesized via a palladium-catalyzed cross-couplingreaction of 1-alkenyl halides or triflates...
Ferdinand Runge 1857: Siemens cycle by Carl Wilhelm Siemens 1859: Pinacolcouplingreaction by Wilhelm Rudolph Fittig 1860–61: Discovery of caesium and rubidium...
liquids processes. Wilhelm Rudolph Fittig: He discovered the pinacolcouplingreaction, mesitylene, diacetyl and biphenyl. Irmgard Flügge-Lotz: She worked...
Robert Bunsen invent an improved spectroscope. Pinacol is discovered through Pinacolcouplingreaction by Wilhelm Rudolph Fittig. John Tyndall discovers...
for their self-healing behaviour. Akin to pinacolcouplings, imines are susceptible to reductive coupling leading to 1,2-diamines. Imine are oxidized...
; Asahara, M.; Muguruma, Y.; Sakurai, H. (2005). "d,l-Selective Pinacol-Type Coupling Using Zinc, Chlorosilane, and Catalytic Amount of Cp2VCl2; dl-1...
reacted with triisopropoxyborane to a boronate ester, then reacted with pinacol and finally reacted with iodobenzene and Tetrakis(triphenylphosphine)palladium(0)...
catalyzed a pinacolcoupling of carbonyls in THF which formed an alkene after reflux with 1,4-dioxane. This is what is now known as the McMurry reaction - McMurry...
Other key reactions encountered in this synthesis are a pinacolcoupling and a Reformatskii reaction. In terms of raw materials the C20 framework is built...
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