Site-Selective Linear Alkylation of Anilides by Cooperative Nickel/Aluminum Catalysis

Shogo Okumura; Takuya Komine; Erika Shigeki; Kazuhiko Semba; Yoshiaki Nakao

doi:10.1002/anie.201710520

Site-Selective Linear Alkylation of Anilides by Cooperative Nickel/Aluminum Catalysis

Angew Chem Int Ed Engl. 2018 Jan 22;57(4):929-932. doi: 10.1002/anie.201710520. Epub 2017 Dec 18.

Authors

Shogo Okumura¹, Takuya Komine¹, Erika Shigeki¹, Kazuhiko Semba¹, Yoshiaki Nakao¹

Affiliation

¹ Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.

PMID: 29193510
DOI: 10.1002/anie.201710520

Abstract

We report meta- and para-selective linear alkylation reactions of anilides with alkenes by nickel/N-heterocyclic carbene (NHC) and aluminum catalysis. With a less bulky NHC, the alkylation reaction of N-methyl-N-phenylcyclohexanecarboxamides proceeded mainly at the meta position. In contrast, a bulky NHC ligand led to the para-selective alkylation of N-sec-alkyl anilides.

Keywords: C−H functionalization; alkenes; aluminum; cooperative catalysis; nickel.

Publication types

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