The fight against entropy is omnipresent in efforts to find new reactions, develop advanced materials and design biologically active molecules. Many of us struggle with this factor and attempt to provide solutions. Take C-H activation as an example. This field has made remarkable strides over the years, but intramolecularity and reliance on the so-called directing groups has been common in finding solutions to some of the longest-standing problems in this field. While attending the FACS meeting in Avignon, I enjoyed listening to the talk by my good friend, Professor Vladimir Gevorgyan of the University of Illinois in Chicago. One of the topics covered in his lecture dealt with silicon tethers that enable the directing element to serve its function and be “erased” towards the end of synthesis using fluoride anion. Alternatively, the C-Si bond could be transformed into something else using cross-coupling or oxidation. The idea of using silicon tether is simple and certainly lifts some of the challenges associated with directing groups that are glued permanently. Below is a link to the paper in Nature Chemistry published by the Gevorgyan lab. There are many other contributions on this topic published by his Chicago team.
amphoteros 