Accounts of Chemical Research
Accounts of Chemical Research
5 years ago

C- and N-Metalated Nitriles: The Relationship between Structure and Selectivity

C- and N-Metalated Nitriles: The Relationship between Structure and Selectivity
Xun Yang, Fraser F. Fleming
Metalated nitriles are exceptional nucleophiles capable of forging highly hindered stereocenters in cases where enolates are unreactive. The excellent nucleophilicity emanates from the powerful inductive stabilization of adjacent negative charge by the nitrile, which has a miniscule steric demand. Inductive stabilization is the key to understanding the reactivity of metalated nitriles because this permits a continuum of structures that range from N-metalated ketenimines to nitrile anions.

Publisher URL: http://dx.doi.org/10.1021/acs.accounts.7b00329

DOI: 10.1021/acs.accounts.7b00329

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