4.8 Article

Iridium(III)-Catalyzed Regioselective B(4)-H Allenylation of o-Carboranes by Ball Milling

Journal

ORGANIC LETTERS
Volume 24, Issue 17, Pages 3128-3133

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00756

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Funding

  1. National Research Foundation of Korea (NRF) - Korean government [2021R1A2C3008862]
  2. National Research Foundation of Korea [2021R1A2C3008862] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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This study presents a novel method for achieving regioselective B(4)-H allenylation of o-carboranes under ball-milling conditions, which cannot be achieved through conventional solution-based reactions.
We disclose an iridium(III)-catalyzed regioselective B(4)-H allenylation of o-carboranes from o-carborane acids and propargyl carbonates under ball-milling conditions. This study sheds light on a novel method to accomplish regioselective B(4)- allenylation of o-carborane that cannot be realized through conventional solution-based reactions. Control experiments, including solution, neat, microwave, and high-temperature reactions, reveal that the B(4)-H allenylation of o-carborane is unique for ballmilling conditions.

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