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Updated: Sep 25, 2025
Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy
Taku Nakayama1, Hidemasa Hikawa1, Shoko Kikkawa1
1Faculty of Pharmaceutical Sciences, Toho University 2-2-1 Miyama, Funabashi Chiba 274-8510 Japan hidemasa.hikawa@phar.toho-u.ac.jp isao.azumaya@phar.toho-u.ac.jp.
Abstract:
A synthetic method for dehydrative N-benzylation promoted by water molecules in heptane using a π-benzylpalladium system has been developed. The presence of water significantly accelerates carbon-nitrogen bond formation, which is accomplished in an atom-economical process to afford the corresponding N-monobenzylated products. A crossover experiment afforded H/D scrambled products, which is consistent with a borrowing hydrogen mechanism. Kinetic isotope effect measurements revealed that benzylic carbon-hydrogen bond cleavage was the rate-determining step.
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