Regioselective Magnesiation and Zincation Reactions of Aromatics and Heterocycles Triggered by Lewis Acids

Autor:	Alexander Kremsmair, Benjamin Heinz, Paul Knochel, Andreas Hess
Rok vydání:	2021
Předmět:	Reaction conditions Chemistry Metalation Continuous flow Organic Chemistry Regioselectivity chemistry.chemical_element General Chemistry Combinatorial chemistry Catalysis Frustrated Lewis pair Reagent Lithium Lewis acids and bases
Zdroj:	Chemistry – A European Journal. 28
ISSN:	1521-3765 0947-6539
Popis:	Mixed TMP-bases (TMP=2,2,6,6-tetramethylpiperidyl), such as TMPMgCl ⋅ LiCl, TMP2 Mg ⋅ 2LiCl, TMPZnCl ⋅ LiCl and TMP2 Zn ⋅ 2LiCl, are outstanding reagents for the metalation of functionalized aromatics and heterocycles. In the presence of Lewis acids, such as BF3 ⋅ OEt2 or MgCl2 , the metalation scope of such bases was dramatically increased, and regioselectivity switches were achieved in the presence or absence of these Lewis acids. Furthermore, highly reactive lithium bases, such as TMPLi or Cy2 NLi, are also compatible with various Lewis acids, such as MgCl2 ⋅ 2LiCl, ZnCl2 ⋅ 2LiCl or CuCN ⋅ 2LiCl. Performing such metalations in continuous flow using commercial setups permitted practical and convenient reaction conditions.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e28d67d06f7e4030773c94f73abd499a https://doi.org/10.1002/chem.202103269 Zobrazit plný text záznamu Plný text