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One-Pot Amidation of Olefins through Pd-Catalyzed Coupling of Alkylboranes and Carbamoyl Chlorides^†

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Yoshizumi Yasui, Sayo Tsuchida, Hideto Miyabe, and Yoshiji Takemoto*

Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan takemoto@pharm.kyoto-u.ac.jp

J. Org. Chem., 2007, 72 (15), pp 5898–5900

DOI: 10.1021/jo070724u

Publication Date (Web): June 20, 2007

†

Dedicated to the memory of Professor Yoshihiko Ito.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

A one-pot synthesis of C₁-elongated amides starting from olefins and carbamoyl chlorides has been developed. Alkylboranes, generated by hydroboration of terminal olefins with 9-BBN-H, underwent smooth coupling with carbamoyl chlorides in the presence of palladium catalyst and Cs₂CO₃.

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Published In Issue July 20, 2007
Received April 6, 2007

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Note

One-Pot Amidation of Olefins through Pd-Catalyzed Coupling of Alkylboranes and Carbamoyl Chlorides^†