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Practical and innate carbon–hydrogen functionalization of heterocycles

Author

Listed:
  • Yuta Fujiwara

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA)

  • Janice A. Dixon

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA)

  • Fionn O’Hara

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA)

  • Erik Daa Funder

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA)

  • Darryl D. Dixon

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA)

  • Rodrigo A. Rodriguez

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA)

  • Ryan D. Baxter

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA)

  • Bart Herlé

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA)

  • Neal Sach

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    La Jolla Laboratories, Pfizer Inc., 10770 Science Center Drive)

  • Michael R. Collins

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    La Jolla Laboratories, Pfizer Inc., 10770 Science Center Drive)

  • Yoshihiro Ishihara

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA)

  • Phil S. Baran

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA)

Abstract

It is shown that zinc sulphinate salts can be used to transfer alkyl radicals to heterocycles, allowing for the mild, direct and operationally simple formation of medicinally relevant carbon–carbon bonds while reacting in a complementary fashion to other innate carbon–hydrogen functionalization methods.

Suggested Citation

  • Yuta Fujiwara & Janice A. Dixon & Fionn O’Hara & Erik Daa Funder & Darryl D. Dixon & Rodrigo A. Rodriguez & Ryan D. Baxter & Bart Herlé & Neal Sach & Michael R. Collins & Yoshihiro Ishihara & Phil S. , 2012. "Practical and innate carbon–hydrogen functionalization of heterocycles," Nature, Nature, vol. 492(7427), pages 95-99, December.
    • Handle: RePEc:nat:nature:v:492:y:2012:i:7427:d:10.1038_nature11680
    DOI: 10.1038/nature11680
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    Cited by:

    1. Emma King-Smith & Felix A. Faber & Usa Reilly & Anton V. Sinitskiy & Qingyi Yang & Bo Liu & Dennis Hyek & Alpha A. Lee, 2024. "Predictive Minisci late stage functionalization with transfer learning," Nature Communications, Nature, vol. 15(1), pages 1-13, December.
    2. Meng Duan & Qianzhen Shao & Qingyang Zhou & Phil S. Baran & K. N. Houk, 2024. "Why •CF2H is nucleophilic but •CF3 is electrophilic in reactions with heterocycles," Nature Communications, Nature, vol. 15(1), pages 1-9, December.

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