Arynes are versatile and reactive building blocks for organic synthesis. Typically, arynes are generated in situ via dehydrohalogenation reactions with strong bases, fluoride displacement of SiMe3 groups, or via elimination of highly energtic precursors such as aryldiazonium carboxylates. None of these routes are broadly compatible with Ti organometallics, and thus we have embarked on a study to find aryne generation conditions that are compatible with early transition metal catalysis. Herein, we report that arynes generated from β-abstraction of zirconocene phenyls can be catalytically and selectively coupled with alkynes by low valent Ti catalysts to generate substituted napthalenes.

Incorporating aryne chemistry into Ti redox catalytic reactions: Ti-catalyzed synthesis of substituted napthalenes via in situ generated arynes

2019 Fall National Meeting

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