Silanol as a Removable Directing Group for the PdII-Catalyzed Direct Olefination of Arenes

Authors

  • Dr. Cong Wang,

    1. Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, 402 N. Blackford St. Indianapolis, IN 46202 (USA), Fax: (+1) 317-274-4701
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  • Prof. Dr. Haibo Ge

    Corresponding author
    1. Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, 402 N. Blackford St. Indianapolis, IN 46202 (USA), Fax: (+1) 317-274-4701
    • Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, 402 N. Blackford St. Indianapolis, IN 46202 (USA), Fax: (+1) 317-274-4701
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Abstract

original image

Need some direction? Silanol was developed as a directing group for the PdII-catalyzed oxidative Heck-type reaction of arenes. A one-pot C[BOND]H activation/desilylation process of benzyldiisopropylsilanol was also demonstrated, providing a powerful approach for the synthesis of ortho-alkenyl-substituted alkylarenes (see scheme). Considering the easily attachable and readily removable properties of the silanol group, this reaction will find broad synthetic applications.

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