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Nucleophilic Substitution at the Guanidine Carbon Center via Guanidine Cyclic Diimide Activation

Taeyang An and Yan Lee*

*Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 08826, Republic of Korea, Email:

T. An, Y. Lee, Org. Lett., 2021, 23, 9163-9167.

DOI: 10.1021/acs.orglett.1c03473

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Guanidine cyclic diimide (GCDI) structures effectively destabilize the resonance structure of the guanidine group. In the presence of acid additives, the guanidine carbon center of GCDIs undergoes nucleophilic substitution reactions with various amines and alcohols.

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ID: J54-Y2021