Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan.
J Am Chem Soc. 2010 Oct 6;132(39):13666-8. doi: 10.1021/ja106514b.
Direct C-4-selective addition of pyridine across alkenes and alkynes is achieved for the first time by nickel/Lewis acid cooperative catalysis with an N-heterocyclic carbene ligand. A variety of substituents on both alkenes and pyridine are tolerated to give linear 4-alkylpyridines in modest to good yields. The addition across styrene, on the other hand, gives branched 4-alkylpyridines. A single example of C-4-selective alkenylation is also described.
镍/路易斯酸协同催化与 N-杂环卡宾配体首次实现了烯烃和炔烃的直接 C-4-选择性加成吡啶反应。烯烃和吡啶上的各种取代基都能容忍，以中等至良好的收率得到线性 4-烷基吡啶。另一方面，苯乙烯的加成得到支化的 4-烷基吡啶。还描述了一个 C-4-选择性烯基化的单一实例。
