Lithium tris magnesate

A metal-iodine exchange has been carried out on all three diazine systems under very mild conditions using lithium tri- -butyl magnesate, although only one substrate from each system was used 3-iodo-6-phenylpyridazine, 4-iodo-2-methylthiopyrimidine and 2-iodopyrazine. The pyridazine example was most problematic, possibly due to solubility problems. Aldehydes, benzophenone and diphenyl disulfide were used as the electrophiles <06SL1586>. 

Lithium tris(iec-butyl)magnesate underwent bromine-magnesium exchange, which was followed by 1,2-migration in the absence of CuCN 2LiCl at room temperature (Scheme 15). However, CuCN 2LiCl was essential for the acylation and allylation. 

Dumouchel, S. Mongin, F. Trecourt, F. Queguiner, G. Synthesis and reactivity of lithium tri(quinolinyl)magnesates. Tetrahedron 2003, 59, 8629-8640. 

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