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

ABSTRACT: 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.

SUBMITTER: Xu TT

PROVIDER: S-EPMC10004367 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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

Xu Tong-Tong TT Zhou Jin-Lan JL Cong Guang-Yuan GY Sheng Jiang-Yi-Hui JY Wang Shi-Qi SQ Ma Yating Y Feng Jian-Jun JJ

Molecules (Basel, Switzerland) 20230226 5

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 ...[more]

PMID: 36903420

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