The search for small-molecule organocatalysts is valuable due to their non-toxic, inexpensive, and moisture/air stable properties with respect to metal-based catalysts. Hydrogen-bonding interactions play an important role for organocatalysis and molecular recognition based on the catalytic activity observed for thioureas and phosphoric acids. Silanols and silanediols are known for their strong hydrogen-bonding capabilities and are frequently used for analytical separations and heterogeneous catalysis. We have demonstrated the catalytic activity of discrete, organic silanediols in carbon-carbon bond forming reactions. Based on this activity, we are studying the mechanism and important role of cooperative hydrogen-bonding in these systems. Discussion will focus on the synthesis of silanols and silanediols as well as their application in the field of organocatalysis.

Silanols and silanediols as hydrogen-bonding organocatalysts

243rd National Meeting (2012)

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