化学
选择性
芳基
卤化物
苯乙酸
组合化学
基质(水族馆)
配体(生物化学)
羧酸盐
反应性(心理学)
卤代芳基
分子
有机化学
催化作用
生物化学
替代医学
受体
病理
地质学
医学
烷基
海洋学
作者
Dong‐Hui Wang,Keary M. Engle,Bing‐Feng Shi,Jin‐Quan Yu
出处
期刊:Science
[American Association for the Advancement of Science (AAAS)]
日期:2010-01-15
卷期号:327 (5963): 315-319
被引量:690
标识
DOI:10.1126/science.1182512
摘要
The Mizoroki-Heck reaction, which couples aryl halides with olefins, has been widely used to stitch together the carbogenic cores of numerous complex organic molecules. Given that the position-selective introduction of a halide onto an arene is not always straightforward, direct olefination of aryl carbon-hydrogen (C-H) bonds would obviate the inefficiencies associated with generating halide precursors or their equivalents. However, methods for carrying out such a reaction have suffered from narrow substrate scope and low positional selectivity. We report an operationally simple, atom-economical, carboxylate-directed Pd(II)-catalyzed C-H olefination reaction with phenylacetic acid and 3-phenylpropionic acid substrates, using oxygen at atmospheric pressure as the oxidant. The positional selectivity can be tuned by introducing amino acid derivatives as ligands. We demonstrate the versatility of the method through direct elaboration of commercial drug scaffolds and efficient syntheses of 2-tetralone and naphthoic acid natural product cores.
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