Tuning the basicity of synergic bimetallic reagents : switching the regioselectivity of the direct dimetalation of toluene from 2,5-to 3,5-positions

Blair, V.L. and Carrella, L.M. and Clegg, W. and Conway, B. and Harrington, R.W. and Hogg, L.M. and Klett, J. and Mulvey, R.E. and Rentschler, Eva and Russo, Luca (2008) Tuning the basicity of synergic bimetallic reagents : switching the regioselectivity of the direct dimetalation of toluene from 2,5-to 3,5-positions. Angewandte Chemie, 47 (33). pp. 6208-6211. ISSN 0044-8249

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Abstract

Meta-meta metalation: Remarkably, toluene can be directly dimanganated or dimagnesiated at the 3,5-positions using bimetallic bases with active Me3SiCH2 ligands (see scheme, blue). In contrast, n-butyl ligands lead to 2,5-metalation (red). tmp=2,2,6,6-tetramethylpiperidide.