利用烷基胺作为亲电试剂通过 C-N 键活化实现镍催化交叉偶联反应。
Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.
机构信息
Department of Chemistry & Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
出版信息
J Am Chem Soc. 2017 Apr 19;139(15):5313-5316. doi: 10.1021/jacs.7b02389. Epub 2017 Apr 5.
Abstract
We developed a strategy to harness alkyl amines as alkylating agents via C-N bond activation. This Suzuki-Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example of a metal-catalyzed cross coupling via C-N bond activation of an amine with an unactivated alkyl group. This reaction enjoys broad scope and functional group tolerance. Primary and secondary alkyl groups can be installed. Preliminary studies suggest a Ni/Ni catalytic cycle.
摘要
我们开发了一种通过 C-N 键活化利用烷基胺作为烷基化试剂的策略。通过 C-N 键活化，仲胺很容易转化为烷基吡啶盐，然后与芳基硼酸进行 Suzuki-Miyaura 交叉偶联反应，这是首例通过 C-N 键活化的金属催化交叉偶联反应，其中胺上的未活化烷基参与反应。该反应具有广泛的适用范围和官能团容忍性，可以实现伯烷基和仲烷基的顺利引入。初步研究表明该反应可能经过 Ni/Ni 催化循环。
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