Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , Singapore 637371, Singapore.
Org Lett. 2015 Feb 6;17(3):442-5. doi: 10.1021/ol503395g. Epub 2015 Jan 9.
An iron-N-heterocyclic carbene catalyst generated from an iron(III) salt, an imidazolinium salt, and a Grignard reagent promotes alkylation and alkenylation reactions at the indole C2-position with vinylarenes and internal alkynes, respectively, via imine-directed C-H activation. The former reaction affords 1,1-diarylalkane derivatives with exclusive regioselectivity. Deuterium-labeling experiments suggest that these reactions involve oxidative addition of the C-H bond to the iron center, insertion of the unsaturated bond into the Fe-H bond, and C-C reductive elimination.
一种由铁(III)盐、咪唑啉盐和格氏试剂生成的铁-N-杂环卡宾催化剂，通过亚胺导向的 C-H 活化，分别促进吲哚 C2-位与乙烯基芳烃和内部炔烃的烷基化和烯基化反应。前者反应以高区域选择性得到 1,1-二芳基烷烃衍生物。氘标记实验表明，这些反应涉及 C-H 键向铁中心的氧化加成、不饱和键插入 Fe-H 键以及 C-C 还原消除。
