Benzene submits to main-group power

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Science  01 Dec 2017:
Vol. 358, Issue 6367, pp. 1132
DOI: 10.1126/science.aaq1314

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The Friedel–Crafts reaction (1), named after its respective French and American pioneers, has long been used to attach alkyl groups to aromatic rings. This reaction is an electrophilic aromatic substitution. Electrophiles are electron-poor species, whereas nucleophiles are electron-rich species. Electron-rich aromatic molecules such as benzene can use their surplus of electrons to react with electron-poor, positively charged species, enabling benzene to exchange one of its hydrogen atoms for the electrophilic group to make a new, substituted benzene. Because “like species repel,” electron-rich species should not react with other electron-rich species, so benzene should never undergo direct nucleophilic alkylation. Nonetheless, on page 1168 of this issue, Wilson et al. (2) report the facile nucleophilic alkylation of benzene accomplished through highly reactive alkylcalcium nucleophiles.