Tetrahedron

Coenzyme-inspired chemistry 1: the C-2 alkylation of 4, 5-dihydroimidazoles

RCF Jones, JR Nichols

Index: Jones, Raymond C.F.; Nichols, John R. Tetrahedron, 2013 , vol. 69, # 20 p. 4114 - 4119

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Abstract

Alkylation of 4, 5-dihydroimidazoles at C-2 is accomplished using a double umpolung of the reactivity of that position, via sulfenylation of a nucleophilic C-2 lithio-species and substitution using an alkyl nucleophile. Arylation via unexpected sulfide contraction from the arylsulfenylation products has also been demonstrated. Taken with dihydroimidazole cleavage protocols, this constitutes a tetrahydrofolate-inspired C1-transfer protocol.