4.8 Article

Intermolecular Allylic C-H Etherification of Internal Olefins

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 45, Pages 14911-14915

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809863

Keywords

C-H functionalization; etherification; intermolecular reactions; rhodium; pi-allyl

Funding

  1. National Science Foundation under the Center for Chemical Innovation in Selective C-H Functionalization [CHE-1700982]
  2. University Research Committee, Emory University
  3. NSF [CHE-1531620]

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Herein we report on the development of an oxidative allylic C-H etherification reaction, utilizing internal olefins and alcohols as simple precursors. Key advances include the use of RhCp* complexes to promote the allylic C-H functionalization of internal olefins and the compatibility of the oxidative conditions with oxidatively sensitive alcohols, enabling the direct etherification reaction. Preliminary mechanistic studies, consistent with C-H functionalization as the rate determining step, are presented.

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