Title: Scaleable Preparation of Functionalized Organometallics <i>via</i> Directed Ortho Metalation Using Mg- and Zn-Amide Bases
Abstract: A range of aryl and heteroaryl organometallics are efficiently prepared in THF via directed ortho metalation by using the previously reported amide bases tmpMgCl·LiCl (tmp = 2,2,6,6-tetramethylpiperidyl), tmp2Mg·2LiCl and tmp2Zn·2MgCl2·2LiCl. These metalation reactions are carried out at 80−100 mmol scale. The unsaturated organometallic compounds undergo smooth reactions with various electrophiles, e.g. additions to carbonyl groups, Pd-catalyzed cross-coupling reactions or Cu-catalyzed acylations. In all cases, the metalation rates have been compared with corresponding small-scale reactions (1−2 mmol). Moreover, a procedure for the recovery of the valuable tmp-H from the aqueous layer is reported.
Publication Year: 2010
Publication Date: 2010-02-01
Language: en
Type: article
Indexed In: ['crossref']
Access and Citation
Cited By Count: 69
AI Researcher Chatbot
Get quick answers to your questions about the article from our AI researcher chatbot