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9.13.5.1.3.1.4 Method 4: Reactions of Aryl and Alkyl Acetylenes in Stoichiometric Metal-Mediated Pyrrole Syntheses

DOI: 10.1055/sos-SD-109-00312

Lubell, W. D.; St-Cyr, D. J.; Dufour-Gallant, J.; Hopewell, R.; Boutard, N.; Kassem, T.; Dörr, A.; Zelli, R.Science of Synthesis Knowledge Updates, (20131184.

To expand the scope beyond electron-poor acetylenes in the [3 + 2]-cycloaddition approaches described in the previous section, stoichiometric metalation of the acetylene component can be used to enhance reactivity. For example, lithium acetylides are sequentially reacted with tungsten (or molybdenum) carbenes and imines to furnish 1-(phenylsulfonyl)pyrroles such as 55 (Scheme 35).[‌78‌,‌79‌]

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