4.8 Article

Access to Branched Allylarenes via Rhodium(III)-Catalyzed C-H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate

Journal

ORGANIC LETTERS
Volume 23, Issue 15, Pages 5719-5723

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01832

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Funding

  1. Guangdong Pharmaceutical University [51377002]
  2. National Natural Science Foundation of China [22001044]
  3. Youth Innovation Talents Project of Colleges and Universities in Guangdong Province [51377201]

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A novel rhodium(III)-catalyzed C-H allylation reaction has been developed using 2-methylidenetrimethylene carbonate as an efficient allylic source, resulting in the synthesis of various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields. Five different directing groups, including oxime, N-nitroso, purine, pyridine, and pyrimidine, were found to be compatible in this reaction.
A rhodium(III)-catalyzed C-H allylation of (hetero)arenes by using 2-methylidenetrimethylene carbonate as an efficient allylic source has been developed for the first time. Five different directing groups including oxime, N-nitroso, purine, pyridine, and pyrimidine were compatible, delivering various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields.

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