铜催化、导向基团辅助的芳环和杂芳环 C-H 键氟化反应。
Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.
机构信息
Department of Chemistry, University of Houston, Houston, Texas 77204-5003, United States.
出版信息
J Am Chem Soc. 2013 Jun 26;135(25):9342-5. doi: 10.1021/ja4047125. Epub 2013 Jun 12.
Abstract
We have developed a method for direct, copper-catalyzed, auxiliary-assisted fluorination of β-sp(2) C-H bonds of benzoic acid derivatives and γ-sp(2) C-H bonds of α,α-disubstituted benzylamine derivatives. The reaction employs a CuI catalyst, a AgF fluoride source, and DMF, pyridine, or DMPU solvent at moderately elevated temperatures. Selective mono- or difluorination can be achieved by simply changing reaction conditions. The method shows excellent functional group tolerance and provides a straightforward way for the preparation of ortho-fluorinated benzoic acids.
摘要
我们开发了一种直接的、铜催化的、辅助辅助的氟化方法，可用于芳基羧酸衍生物的β-sp(2) C-H 键和α,α-二取代苄胺衍生物的γ-sp(2) C-H 键。该反应采用 CuI 催化剂、AgF 氟源以及 DMF、吡啶或 DMPU 溶剂，在中等升高的温度下进行。通过简单改变反应条件，可以实现选择性的单氟化或双氟化。该方法具有出色的官能团耐受性，并为制备邻位氟化苯甲酸提供了一种直接的方法。
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