Trimethylsilyl (TMS) alkynes, have been found to serve as selective cross coupling partners in Ti-catalyzed [2+2+1] multicomponent pyrrole synthesis. Reactions between TMS protected alkynes, internal alkynes and diazenes could have ten potential pyrrole products, but in almost all examples, a single 2-trimethylsilylpyrrole cross-product regioisomer accounts for up to 90% of the product mixture. After reactions, 2-TMS pyrroles can be easily hydrolyzed and/or functionalized. An investigation of the scope and key factors which lead to such high chemo- and regioselectivity based on mechanistic and computation studies will be presented. This strategy provides a convenient methodology to synthesize multisubstituted pyrroles with a variety of substrates and good yields.

TMS-protected alkynes as selective cross coupling partners in Ti catalyzed [2+2+1] pyrrole synthesis

255th National Meeting (2018)

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