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Iridium-Catalyzed Branch-Selective Hydroalkylation of Simple Alkenes with Malonic Amides and Malonic Esters

Takahiro Sawano, Masaki Ono, Ami Iwasa, Masaya Hayase, Juri Funatsuki, Ayumu Sugiyama, Eri Ishikawa, Takeshi Yoshikawa, Ken Sakata* and Ryo Takeuchi*

*Toho University, Funabashi, Chiba 274-8510; Aoyama Gakuin University, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan, Email: ken.sakataphar.toho-u.ac.jp, takeuchichem.aoyama.ac.jp

T. Sawano, M. Ono, A. Iwasa, M. Hayase, J. Funatsuki, A. Sugiyama, E. Ishikawa, T. Yoshikawa, K. Sakata, R. Takeuchi, J. Org. Chem., 2023, 88, 1545-1559.

DOI: 10.1021/acs.joc.2c02599


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Abstract

Iridium catalyzes a branch-selective hydroalkylation of simple aliphatic and aromatic alkenes with malonic amides and malonic esters under neutral reaction conditions. A substrates bearing bromine, chlorine, ester, 2-thienylcarboxylate, silyl, and phthalimide groups are suitable for this hydroalkylation. Selective transformations of hydroalkylated products to 1,3-diamines or monoamides are reported.

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proposed mechanism



Key Words

active methylene compounds (alkylation, benzylation), amides (alkylation), decarboxylation


ID: J42-Y2023