Metal-less Methodology: making carbon-carbon bonds using purely organic reaction components.

One of the hallmarks of modern organic synthesis is the heavy reliance on metal-based catalysts and reagents. Modern metal-based synthetic methodology has proved to be very powerful in mediating the formation of carbon-carbon bonds in ways not possible by the traditional methods you learned in Organic Chemistry I and II. But, there is always room for improvements and new developments. For instance, many metals are expensive, toxic or environmentally problematic, or difficult to work with due to extreme air or water sensitivity. There has been a recent surge in the development of new synthetic methods that don't rely on metals. Some of these methods mimic known metal-based methods, others hark back to traditional metal-less transformations, with new twists (usually the twist is stereoselectivity). Dave and Gretchen spent last year in the laboratory of Professor Karl Anker Jørgensen, at Aarhus University, Aarhus, Denmark. The Jørgensen group is a leader in developing new metal-less synthetic methods - especially those involving so-called "organocatalysis". Dave and Gretchen will discuss a number of projects they worked on, including the development of a metal-less alternative to the venerable metal-catalyzed Sonogashira coupling and an organocatalytic aldol reaction of potential biological importance.