Remote Steric Control for Undirected meta-Selective C–H Activation of Arenes

Laurean Ilies and Sobi Asako present the steric control for undirected C–H activation reactions of arenes.

According to Dr. Laurean Ilies from the RIKEN Center for Sustainable Resource Science (Saitama, Japan), a major goal of modern synthetic chemistry is the creation of organic molecules in the most straightforward and efficient manner possible. He said that “the use of a metal catalyst to directly introduce functionality into a simple or complex organic molecule (transition-metal-catalyzed C–H activation) has received much attention, but a serious problem arises – even simple organic molecules have many C–H bonds and steering the catalytic species towards the desired site is difficult.” The research described here by the group of Dr. Laurean Ilies and Dr. Sobi Asako provides a new solution to the selectivity problem. Inspired by the lock-and-key model of enzymatic catalysis, the authors designed a new catalytic system which creates a molecular pocket that fits an arene substrate only in a determined orientation, thus controlling the selectivity. They demonstrated this concept for the meta-selective functionalization of simple arenes such as alkylbenzenes, anilines, phenols, etc. and for the late-stage selective functionalization of complex drug molecules.

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