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Synthesis 2018; 50(18): 3615-3633
DOI: 10.1055/s-0036-1591953
DOI: 10.1055/s-0036-1591953
short review
In Situ ‘Trans-Metal Trapping’: An Efficient Way to Extend the Scope of Aromatic Deprotometalation
Université de Rennes 1; Ministère de l’Enseignement supérieur et de la Recherche scientifique Algérien; Centre National de la Recherche Scientifique (PICS SYNAROM)Further Information
Publication History
Received: 05 February 2018
Accepted: 12 February 2018
Publication Date:
08 March 2018 (online)
Published as part of the Special Section on the Main Group Metal Chemistry Symposium
Abstract
Deprotometalation is an efficient method to functionalize regioselectively aromatic compounds including heterocycles. This short review shows how it is possible to intercept aryllithiums (and other polar arylmetals) as soon as they are formed by in situ ‘trans-metal trapping’. The approach avoids long contact between aryllithiums and sensitive substrates. In addition, it allows less activated substrates to be deprotonated by non-nucleophilic lithium amides. While using chlorosilanes and borates still arouses the interest of chemists, more recently, methods based on zinc, aluminum and gallium have appeared, enabling this chemistry to grow dramatically.
1 Introduction
2 Silicon-Based In Situ Traps
3 Boron-Based In Situ Traps
4 Zinc-Based In Situ Traps
5 Aluminum- and Gallium-Based In Situ Traps
6 Other In Situ Traps
7 Continuous-Flow In Situ ‘Trans-Metal Trapping’
8 Conclusion
-
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Note that lithium chloride, formed by using in situ traps such as chlorotrimethylsilane and zinc chloride, can also impact the reaction rate. See for example:
In the framework of this short review, we discarded studies on the lithium–cadmium base ‘(TMP)3CdLi’ in spite of a probably similar behavior, see: