In situ 'Trans-metal Trapping': an Efficient Way to Extend the Scope of Aromatic Deprotometalation

Nahida Brikci-Nigassa (1) , Ghenia Bentabed-Ababsa (1) , Florence Mongin (2) , William Erb (2)

1 LSOA - Laboratoire de Synthèse Organique Appliquée
2 ISCR - Institut des Sciences Chimiques de Rennes

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, methods based on zinc, aluminum and gallium more recently appeared, enabling this chemistry to grow dramatically.

Keywords: in situ trap; transmetalation; silicon; boron; aromatic compounds; lithium amides; deprotometalation; zinc

Domains: Chemical Sciences; Organic chemistry

Nahida Brikci-Nigassa, Ghenia Bentabed-Ababsa, Florence Mongin, William Erb. In situ 'Trans-metal Trapping': an Efficient Way to Extend the Scope of Aromatic Deprotometalation. Synthesis: Journal of Synthetic Organic Chemistry, 2018, 50 (18), pp.3615-3633. ⟨10.1055/s-0036-1591953⟩. ⟨hal-01902075⟩