Tetrahedron Letters

Grignard allylic substitution catalyzed by imidazol-2-ylidene-and imidazol-4-ylidene-magnesium complexes

S Okamoto, H Ishikawa, Y Shibata, Y Suhara

Index: Okamoto, Sentaro; Ishikawa, Hiroyuki; Shibata, Yoshimi; Suhara, Yu-Ichiro Tetrahedron Letters, 2010 , vol. 51, # 43 p. 5704 - 5707

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Citation Number: 5

Abstract

In the presence of a catalytic amount of 1, 2-disubstituted or 1, 2, 3-trisubstituted imidazolium salts, γ-substituted allyl chlorides reacted with alkyl Grignard reagents to undergo substitution reactions in an SN2′-selective fashion, where the magnesium ate complexes [(N-heterocyclic carbene-MgR3)−(MgX)+] of imidazol-2-ylidenes or imidazol-4-ylidenes, generated in situ, were postulated as the active species. It was observed that the reactions ...