One-pot amidation of olefins through Pd-catalyzed coupling of alkylboranes and carbamoyl chlorides

Yoshizumi Yasui; Sayo Tsuchida; Hideto Miyabe; Yoshiji Takemoto

doi:10.1021/jo070724u

One-pot amidation of olefins through Pd-catalyzed coupling of alkylboranes and carbamoyl chlorides

J Org Chem. 2007 Jul 20;72(15):5898-900. doi: 10.1021/jo070724u. Epub 2007 Jun 20.

Authors

Yoshizumi Yasui¹, Sayo Tsuchida, Hideto Miyabe, Yoshiji Takemoto

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.

PMID: 17580905
DOI: 10.1021/jo070724u

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry*
Amides / chemistry*
Boranes / chemistry*
Catalysis
Chlorides / chemistry*
Palladium / chemistry*

Substances

Alkenes
Amides
Boranes
Chlorides
Palladium