锌催化剂作用下吡啶、甲基吡啶和喹啉的硅烷化反应
Silylation of Pyridine, Picolines, and Quinoline with a Zinc Catalyst.
作者信息
Prybil Joshua W, Wallace Rodney, Warren Alexandra, Klingman Jordan, Vaillant Romane, Hall Michael B, Yang Xin, Brennessel William W, Chin Robert M
机构信息
Department of Chemistry and Biochemistry, University of Northern Iowa, Cedar Falls, Iowa 50614-0423, United States.
École nationale supérieure de chimie de Rennes, Sciences Chimiques de Rennes, Rennes, Bretagne 35700, France.
出版信息
ACS Omega. 2020 Jan 10;5(3):1528-1539. doi: 10.1021/acsomega.9b03317. eCollection 2020 Jan 28.
Zn(OTf) (OTf = trifluoromethanesulfonate) catalyzes the silylation of pyridine, 3-picoline, and quinoline to afford the silylated products, where the silyl groups are to the nitrogen. The isolated yields of the products range from 41 to 26%. The 2- and 4-picolines yielded the silylmethylpyridines, where the CH groups were silylated instead of the ring. The pyridine silylation can occur via two separate pathways, involving either a 1,4- or a 1,2-hydrosilylation of pyridine as the first step. A byproduct of the pyridine silylation is a head-to-tail dimerization of -silyl-1,4-dihydropyridine to form a diazaditwistane molecule.
三氟甲磺酸锌（OTf = 三氟甲磺酸盐）催化吡啶、3 - 甲基吡啶和喹啉的硅烷化反应，得到硅烷化产物，其中硅烷基连接在氮原子上。产物的分离产率为41%至26%。2 - 甲基吡啶和4 - 甲基吡啶生成了硅烷基甲基吡啶，其中甲基被硅烷化而非环。吡啶的硅烷化反应可通过两条不同途径发生，第一步涉及吡啶的1,4 - 氢硅烷化或1,2 - 氢硅烷化。吡啶硅烷化反应的一个副产物是β - 硅烷基 - 1,4 - 二氢吡啶的头对头二聚化，形成一个二氮杂双扭曲烷分子。
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