烷基化
化学
催化作用
钯
表面改性
基础(拓扑)
组合化学
选择性
基质(水族馆)
药物化学
二聚体
立体化学
有机化学
数学分析
海洋学
数学
物理化学
地质学
作者
Jinquan Zhang,Shuaizhong Zhang,Hongbin Zou
出处
期刊:Organic Letters
[American Chemical Society]
日期:2021-04-21
卷期号:23 (9): 3466-3471
被引量:9
标识
DOI:10.1021/acs.orglett.1c00903
摘要
The functionalization of remote unactivated C(sp3)–H and the reaction selectivity are among the core pursuits for transition-metal catalytic system development. Herein, we report Pd-catalyzed γ-C(sp3)–H-selective alkylation and alkenylation with removable 7-azaindole as a directing group. Acid and base were found to be the decisive regulators for the selective alkylation and alkenylation, respectively, on the same single substrate under otherwise the same reaction conditions. Various acrylates were compatible for the formation of C(sp3)–C(sp3) and C(sp3)–C(sp2) bonds. The alkenylation protocol could be further extended to acrylates with natural product units and α,β-unsaturated ketones. The preliminary synthetic manipulation of the alkylation and alkenylation products demonstrates the potential of this strategy for structurally diverse aliphatic chain extension and functionalization. Mechanistic experimental studies showed that the acidic and basic catalytic transformations shared the same six-membered dimer palladacycle.
科研通智能强力驱动
Strongly Powered by AbleSci AI