Indium-Triflate-Catalyzed Ritter Reaction in Liquid Sulfur Dioxide
The use of liquid sulfur dioxide as a reaction solvent facilitates the Ritter reaction between alcohols and nitriles. In(OTf)3 was found to be a viable catalyst for this transformation. The newly developed catalytic conditions for the Ritter reaction were successfully applied to the synthesis of various amides, which were formed in good to excellent yields. The catalytic activation of secondary alcohols for Ritter reactions in liquid sulfur dioxide was also found to be effective.
Posevins, Daniels,Suta, Krista,Turks, Maris
supporting information
p. 1414 - 1419
(2016/03/19)
Stereoretentive copper(II)-catalyzed ritter reactions of secondary cycloalkanols
A Ritter-like coupling reaction of cyclic alcohols and both aryl and alkyl nitriles to form amides catalyzed by copper(II) triflate is described. These reactions proceed in good yields under mild and often solvent-free conditions. With 2-and 3-substituted
Al-Huniti, Mohammed H.,Lepore, Salvatore D.
supporting information
p. 3071 - 3076
(2014/03/21)
A direct and stereoretentive synthesis of amides from cyclic alcohols
Chlorosulfites prepared in situ using thionyl chloride react with nitrile complexes of titanium(IV) fluoride to give a one-pot conversion of alcohols into amides. For the first time, amides are obtained from cyclic alcohols with stereoretention. Critical to the design of these new TiIV reactions has been the use of little-explored TiIV nitrile complexes that are thought to chelate chlorosulfites in the transition state tocreate a carbocation that is rapidly captured by the nitrile nucleophile through a front-side attack mechanism.
Mondal, Deboprosad,Bellucci, Luca,Lepore, Salvatore D.
p. 7057 - 7061
(2012/01/03)
Efficient and stereodivergent electrochemical synthesis of optically pure menthylamines
The cathode directs the way to the epimeric menthylamines. The reduction of menthone oxime on a Hg cathode generates (-)-menthylamine as the major product, whereas a Pb cathode gives access to (+)-neomenthylamine (see scheme). Insitu decoration of the Pb cathode by small amounts of additives results in clean and quantitative conversions. Furthermore, Pb corrosion is completely prevented in this practical method. Copyright
Kulisch, Joern,Nieger, Martin,Stecker, Florian,Fischer, Andreas,Waldvogel, Siegfried R.
p. 5564 - 5567
(2011/07/30)
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