Tetrahedron

Effets du solvant et du complexant sur la regioselectivite de la metallation. Cas de la (furyl-2)-2 pyridine

P Ribereau, G Queguiner

Index: Ribereau, P.; Queguiner, G. Tetrahedron, 1983 , vol. 39, # 21 p. 3593 - 3602

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Citation Number: 17

Abstract

Lithiation of 2-(2-furyl) pyridine with n-butyllithium is dependent upon the nature of the solvent, lithium complexant, and temperature. ω-Lithiation of the furan ring increases with the importance of the solvation of the lithium atom (TMEDA> THF> ether> hexane). The α substituted derivative, which is the thermodynamically controlled product, is obtained in ether with a good yield either with DABCO-BuLi or by HMPT catalyzed migration of lithium ...