Photocatalyzed [2 + 2 + 2]-cycloaddition of nitriles with acetylene: an effective method for the synthesis of 2-pyridines under mild conditions.

Barbara Heller, Bernd Sundermann, Helmut Buschmann, Hans-Joachim Drexler, Jingsong You, Ulrike Holzgrabe, Eberhard Heller, Günther Oehme

Index: J. Org. Chem. 67(13) , 4414-22, (2002)

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Abstract

The photocatalyzed [2 + 2 + 2]-cycloaddition of nitriles with 2 equiv of acetylene to 2-pyridines can be carried out under mild conditions and represents a valuable extension to common synthetical methods. For the ideal wavelength range (350-500 nm), lamps as well as sunlight can be used. Working at room temperature and in organic solvents such as toluene or hexane as well as in water gives satisfying results in many cases. However, it is also possible to vary the solvent and the reaction temperature of the photocatalyzed synthesis and to choose, with respect to the specific substrate, specific requirements for this particular reaction and general requirements of the method. This simple and selective method derives its potential mainly from the large variety of applicable nitriles. Suitable substrates include (functionalized) aliphatic and aromatic nitriles as well as cyanamides derived from secondary amines.