o-Tolyl-substituted tetrahydrofurans undergo highly regioselective ring opening with the concomitant formation of new C–C bonds as the result of a lateral lithiation reaction. This reaction provides a new method for the synthesis of functionalised primary alcohols and can be run directly in protic eutectic mixtures as benign reaction media at 0 °C and under air, competitively with protonolysis.

Unexpected lateral-lithiation-induced alkylative ring opening of tetrahydrofurans in deep eutectic solvents: synthesis of functionalised primary alcohols

PERNA, FILIPPO;Salomone A;CAPRIATI, Vito
2015

Abstract

o-Tolyl-substituted tetrahydrofurans undergo highly regioselective ring opening with the concomitant formation of new C–C bonds as the result of a lateral lithiation reaction. This reaction provides a new method for the synthesis of functionalised primary alcohols and can be run directly in protic eutectic mixtures as benign reaction media at 0 °C and under air, competitively with protonolysis.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11586/139581
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