Palladium-Catalyzed Asymmetric C(sp3 )-H Allylation of 2-Alkylpyridines

Ryo Murakami; Kentaro Sano; Tomohiro Iwai; Tohru Taniguchi; Kenji Monde; Masaya Sawamura

doi:10.1002/anie.201802821

Palladium-Catalyzed Asymmetric C(sp³ )-H Allylation of 2-Alkylpyridines

Angew Chem Int Ed Engl. 2018 Jul 20;57(30):9465-9469. doi: 10.1002/anie.201802821. Epub 2018 Jun 22.

Authors

Ryo Murakami¹, Kentaro Sano¹, Tomohiro Iwai¹, Tohru Taniguchi², Kenji Monde², Masaya Sawamura¹

Affiliations

¹ Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, 060-0810, Japan.
² Frontier Research Center for Advanced Material and Life Science, Faculty of Advanced Life Science, Hokkaido University, Sapporo, 001-0021, Japan.

PMID: 29863762
DOI: 10.1002/anie.201802821

Abstract

The palladium-catalyzed asymmetric side-chain C(α)-allylation of 2-alkylpyridines, without using an external base, was developed. The high linear selectivities and enantioselectivities were achieved using new chiral diamidophosphite monodentate ligands. Given that the reaction conditions do not require an external base, this catalyst system enabled chemoselective C(α)-allylation of 2-alkylpyridines containing α-carbonyl C-H bonds, which are more acidic than α-pyridyl C-H bonds.

Keywords: C−H activation; allylation; asymmetric catalysis; ligand design; palladium.

Publication types

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