School of Chemistry & Chemical Engineering, South China University of Technology , Wushan Road - 381, Guangzhou 510641, People's Republic of China.
Org Lett. 2016 Jul 1;18(13):3174-7. doi: 10.1021/acs.orglett.6b01390. Epub 2016 Jun 14.
A new benzylation protocol, enabling straightforward access to β-benzylated quinolines, has been demonstrated. By employing readily available [RuCl2(p-cymene)]2 as a catalyst and O2 as a sole green oxidant, various 1,2,3,4-tetrahydroquinolines were efficiently converted in combination with aryl aldehydes into desired products in a step- and atom-economic fashion together with the advantages of excellent functional group tolerance and chemoselectivity, offering an important basis for the transformation of saturated N-heterocycles into functionalized N-heteroaromatics via a dehydrogenative cross-coupling strategy. Mechanistic investigations support that the reaction undergoes a monodehydrogenation-triggered β-benzylation mode.
已证明一种新的苄基化方案，可直接获得β-苄基化喹啉。通过使用易得的[RuCl2(p-cymene)]2作为催化剂和 O2 作为唯一的绿色氧化剂，各种 1,2,3,4-四氢喹啉与芳醛结合，以一步原子经济性方式有效地转化为所需产物，具有出色的官能团耐受性和化学选择性，为通过脱氢交叉偶联策略将饱和 N-杂环转化为功能化 N-杂芳烃提供了重要基础。机理研究支持该反应经历单脱氢引发的β-苄基化模式。
