原位阴离子屏蔽：区域选择性金属化的导向邻位和迭代金属化途径，用于多官能化的 7-氮杂吲哚。

In situ anionic shielding for regioselective metalation: directed peri and iterative metalation routes to polyfunctionalized 7-azaindoles.

机构信息

Department of Chemistry, Queen's University, Kingston, Ontario, Canada.

出版信息

Angew Chem Int Ed Engl. 2012 Mar 12;51(11):2722-6. doi: 10.1002/anie.201108016. Epub 2012 Feb 1.

DOI:10.1002/anie.201108016

Abstract

Strolling the ring: a general regioselective directed peri(C4)-metalation route to 1 through an in situ N-anionic protection of C2 is reported. The azaindoles may be elaborated by directed ortho metalation (DoM) and Suzuki coupling to more complex heterocyclic systems. An iterative ring-walk DoM sequence furnishes the exhaustively substituted 2. DMG=directed metalation group, TMEDA=N,N,N',N'-tetramethylethylenediamine, TMS=trimethylsilyl.

摘要

漫步环上

通过 C2 的原位 N-阴离子保护，报道了一种通用的区域选择性导向的peri(C4)-金属化途径 1。通过定向邻位金属化（DoM）和铃木偶联，可以将氮茚类化合物进一步转化为更复杂的杂环体系。迭代的环行走 DoM 序列提供了完全取代的 2。DMG=导向金属化基团，TMEDA=N,N,N',N'-四甲基乙二胺，TMS=三甲基硅基。