Alkali-metal mediated zincation of N-heterocyclic substrates using the lithium zincate complex, (THF)Li(TMP)Zn(tBu)(2) and applications in in situ cross coupling reactions

Abstract This study investigates the ability of the mixed-metal reagent [Li(TMP)Zn( t Bu) 2 ] 1 to promote direct Zn–H exchange reactions (zincations) of a wide range of N -heterocyclic molecules. The generated metallated intermediates from these reactions are intercepted with I 2 and some of them are also employed as precursors in Pd-catalysed Negishi cross-coupling applications. A comparison with recent precedents in metallation chemistry reveals that for some of these heterocycles, 1 allows improved conversions, under milder conditions and in certain cases, even gives unique regioselectivities.