Molecules (Feb 2023)

Boron Lewis Acid Catalysis Enables the Direct Cyanation of Benzyl Alcohols by Means of Isonitrile as Cyanide Source

  • Tong-Tong Xu,
  • Jin-Lan Zhou,
  • Guang-Yuan Cong,
  • Jiang-Yi-Hui Sheng,
  • Shi-Qi Wang,
  • Yating Ma,
  • Jian-Jun Feng

DOI
https://doi.org/10.3390/molecules28052174
Journal volume & issue
Vol. 28, no. 5
p. 2174

Abstract

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The development of an efficient and straightforward method for cyanation of alcohols is of great value. However, the cyanation of alcohols always requires toxic cyanide sources. Herein, an unprecedented synthetic application of an isonitrile as a safer cyanide source in B(C6F5)3-catalyzed direct cyanation of alcohols is reported. With this approach, a wide range of valuable α-aryl nitriles was synthesized in good to excellent yields (up to 98%). The reaction can be scaled up and the practicability of this approach is further manifested in the synthesis of an anti-inflammatory drug, naproxen. Moreover, experimental studies were performed to illustrate the reaction mechanism.

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