铱催化的醇与甲基喹啉的烷基化反应。

Iridium-catalyzed alkylation of methylquinolines with alcohols.

机构信息

Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka 564-8680, Japan.

出版信息

J Org Chem. 2012 Oct 19;77(20):9429-33. doi: 10.1021/jo3019347. Epub 2012 Oct 3.

DOI:10.1021/jo3019347

PMID:23013149

Abstract

Iridium-catalyzed alkylation of methylquinolines at the methyl substituent was achieved using alcohols as alkylating agents. The reaction proceeded through a transfer hydrogenation pathway from the alcohol to the Ir complex, affording an aldehyde and Ir-H species, followed by base-assisted aldol condensation and hydrogenation. This method provides an atom-economical and convenient route to alkylquinolines from easily accessible methylquinolines.

摘要

铱催化的甲基喹啉在甲基取代基上的烷基化反应使用醇作为烷基化试剂。反应通过醇向铱配合物的转移氢化途径进行，得到醛和 Ir-H 物种，然后进行碱辅助的羟醛缩合和氢化。该方法提供了一种从易得的甲基喹啉到烷基喹啉的原子经济性和方便的途径。