Remote Control by Steric Effects

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Science  21 Feb 2014:
Vol. 343, Issue 6173, pp. 850-851
DOI: 10.1126/science.1250335

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The benzene ring is one of the most prevalent structural motifs found in organic compounds, and the development of efficient and selective methods for the synthesis of benzene derivatives has attracted the interest of organic chemists for more than a century. When introducing a new substituent onto substituted benzene derivatives, one critical issue is regioselectivity (i.e., which particular C-H bonds will react). One strategy for addressing this issue is to use bulky substituents on the ring—which often are added deliberately—to limit access of a reagent or a catalyst to adjacent C-H bonds, thus directing the reaction to other positions. On page 878 of this issue, Cheng and Hartwig (1) report that the steric bulk of the substituent can be used to achieve an unusually high selectivity among the C-H bonds that are located at more remote positions of the benzene ring.