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

作者：Blair Victoria L^*; Blakemore David C; Hay Duncan; Hevia Eva; Pryde David C

来源：Tetrahedron Letters, 2011, 52(36): 4590-4594.

DOI：10.1016/j.tetlet.2011.06.090

• Metallation
• Zincation
• N-Heterocycles
• Lithium
• Mixed-metal reagents

This study investigates the ability of the mixed-metal reagent [Li(TMP)Zn(tBu)(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.

• 出版日期2011-9-7