Pd(II)催化的单取代芳基的对位选择性 C-H 芳基化反应。
Pd(II)-catalyzed para-selective C-H arylation of monosubstituted arenes.
机构信息
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, United States.
出版信息
J Am Chem Soc. 2011 Sep 7;133(35):13864-7. doi: 10.1021/ja206572w. Epub 2011 Aug 16.
Abstract
Pd-catalyzed highly para-selective C-H arylation of monosubstituted arenes (including toluene) is developed for the first time using an F(+) reagent as a bystanding oxidant. This finding provides a new retrosynthetic disconnection for para-substituted biaryl synthesis via C-H/C-H cross-coupling.
摘要
首次开发了使用 F(+)试剂作为旁观氧化剂的 Pd 催化的单取代芳基（包括甲苯）的高对位选择性 C-H 芳基化反应。这一发现为通过 C-H/C-H 交叉偶联合成对位取代联芳基提供了新的逆合成切断方法。
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1
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2
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J Am Chem Soc. 2011 Mar 30;133(12):4455-64. doi: 10.1021/ja1097918. Epub 2011 Mar 7.
3
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4
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