Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 15, Pages 5693-5696Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500102
Keywords
homogeneous catalysis; radicals; reductive coupling; titanium; umpolung
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Funding
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft (DFG) [STR 1150/3-1]
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A new method for titanium-catalyzed reductive umpolung reactions is reported that overcomes the traditional requirement for a stoichiometric metallic reductant. With N, N'-disilylated tetramethyldihydropyrazine as a potent organic reducing agent, reductive carbonyl-nitrile, enone-acrylonitrile and pinacol coupling reactions can be achieved in good yields and stereoselectivities. [Cp2TiI2] is a superior catalyst to [Cp2TiCl2], which is rationalized by a faster generation of the active catalyst [Cp2TiI]. A mechanism is proposed that is in agreement with the experimental results.
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