4.7 Article

Photo-Induced Cross-Dehydrogenative Alkylation of Heteroarenes with Alkanes under Aerobic Conditions

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 24, Pages 17816-17832

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02125

Keywords

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Funding

  1. National Key R&D Program of China [2019YFC1604605]
  2. Key Industrial Technology Innovation Project of Suzhou [SYG201919]
  3. Ministry of Education, Singapore [MOE2017-T2-2-110]
  4. Agency for Science, Technology and Research (A*STAR) [A1883c0011, A1983c0038]
  5. National Research Foundation
  6. Prime Minister's Office of Singapore under its Competitive Research Program [NRF-CRP232019-0002]
  7. Prime Minister's Office of Singapore under NRF Investigatorship Programme [NRF-NRFI05-2019-0003]
  8. National Natural Science Foundation of China [22178078, 21871071]
  9. Major Scientific and Technological Innovation Project of Zhejiang [2019C01081]

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A Minisci-type cross-dehydrogenative alkylation was reported using cerium chloride as a photocatalyst and air as an oxidant, showing excellent tolerance to functional groups and suitability for both heteroarene and alkane substrates, providing an alternative approach for late-stage functionalization of valuable substrates.
We report a Minisci-type cross-dehydrogenative alkylation in an aerobic atmosphere using abundant and inexpensive cerium chloride as a photocatalyst and air as an oxidant. This photoreaction exhibits excellent tolerance to functional groups and is suitable for both heteroarene and alkane substrates under mild conditions, generating the corresponding products in moderate-to-good yields. Our method provides an alternative approach for the late-stage functionalization of valuable substrates.

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