Recent Advances in the Synthesis of Cyanides Enabled by N-Heterocyclic Carbene Catalysis

doi:10.6023/cjoc202303002

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3135-3145.DOI: 10.6023/cjoc202303002 Previous Articles Next Articles

氮杂环卡宾催化合成氰基化合物的研究进展

蔡远林^a, 吕亚^a, 聂桂花^a, 金智超^a^,^*(), 池永贵^a^,^b^,^*()

a 贵州大学精细化工研究开发中心贵州大学绿色农药全国重点实验室绿色农药与农业生物工程教育部重点实验室贵阳 550025
b 南洋理工大学化学化工与生物技术学院新加坡 637371

收稿日期:2023-03-01 修回日期:2023-04-10 发布日期:2023-05-05
基金资助:
国家自然科学基金(21961006); 国家自然科学基金(32172459); 国家自然科学基金(22071036); 贵州省教育厅不对称合成与药物分子前沿科学中心(KY(2020)004); 贵州大学中国高校学科人才引进计划(D20023); 新加坡国家研究基金(NRFNRFI2016-06); 竞争研究计划(NRFCRP22-2019-0002); 新加坡教育部(RG7/20); 新加坡教育部(RG5/19); 新加坡教育部(MOE2019-T2-2-117); 及新加坡教育部(MOE2018-T3-1-003)

Recent Advances in the Synthesis of Cyanides Enabled by N-Heterocyclic Carbene Catalysis

Yuanlin Cai^a, Ya Lü^a, Guihua Nie^a, Zhichao Jin^a(), Yonggui Chi^a^,^b()

a Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, National Key Laboratory of Green Pesticide, Center for R&D of Fine Chemicals, Guizhou University, Guiyang 550025
b School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371

Received:2023-03-01 Revised:2023-04-10 Published:2023-05-05
Contact: * E-mail: zcjin@gzu.edu.cn;robinchi@ntu.edu.sg
Supported by:
National Natural Science Foundation of China(21961006); National Natural Science Foundation of China(32172459); National Natural Science Foundation of China(22071036); Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province(KY(2020)004); Program of Introducing Talents of Discipline to Universities of China at Guizhou University(D20023); Singapore National Research Foundation under Its NRF Investigatorship(NRFNRFI2016-06); Competitive Research Program(NRFCRP22-2019-0002); Singapore Ministry of Education under Its MOE AcRF Tier 1 Award(RG7/20); Singapore Ministry of Education under Its MOE AcRF Tier 1 Award(RG5/19); MOE AcRF Tier 2 Award(MOE2019-T2-2-117); MOE AcRF Tier 3 Award(MOE2018-T3-1-003)

Cyanide compounds are not only widely found in medicine and pesticide molecules, but also a class of important intermediates. The traditional method for the synthesis of cyano compounds is to use the simplest cyanide reagents such as sodium cyanide, potassium cyanide and hydrocyanic acid, but the toxicity and instability of cyanide reagents have limited its application in synthesis. Therefore, the development of organic cyanide reagents and cyanide-free reagents for the construction of cyano compounds has attracted much attention. N-Heterocyclic carbene (NHC) is a kind of effective small-molecule organocatalysts. A series of catalytic activation modes enabled by NHC have been developed for the formation of various carbon-carbon (C—C) and carbon-heteroatom (C—X) bonds. With the purpose of attracting much attention to this research field and bringing new ideas into the development of the NHC organocatalytic reactions, the catalytic reactions for the construction of cyano compounds enabled by NHC with organic cyanide reagents or cyanide-free reagents are summarized.

Key words: N-heterocyclic carbene (NHC), organic cyanide reagent, cyanide-free reagent, cyanation reaction, cyanide compound

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Yuanlin Cai, Ya Lü, Guihua Nie, Zhichao Jin, Yonggui Chi. Recent Advances in the Synthesis of Cyanides Enabled by N-Heterocyclic Carbene Catalysis[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3135-3145.

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Fig. & Tab. 15

Figure 1. Drugs and pesticides containing cyano functional groups

Scheme 1. Cyanidation of TMSCN with aldehydes catalyzed by NHC

Scheme 2. Asymmetric catalytic cyanidation of TMSCN with aldehydes by NHC

Scheme 3. Cyanidation of TMSCN with aldehydes or ketones catalyzed by NHC

Scheme 4. Highly efficient silylcyanation of aldehydes, ketones or imines catalyzed by NHC

Scheme 5. Study on the mechanism of NHC-catalyzed cyanidation of TMSCN with aldimine

Scheme 6. NHC-catalyzed 1,6-conjugate addition reaction of TMSCN with para-quinone methyl compounds

Scheme 7. NHC catalyzed cyanation reaction of carbonyl compounds with ethyl cyanoformate and acetyl cyanide

Scheme 8. Cyanidation of α-keto esters catalyzed by NHC

Scheme 9. NHC-catalyzed cyanidation of aldimines

Scheme 10. NHC-catalyzed cyanidation of diethyl cyanophosphonate with carbonyl compounds

Scheme 11. NHC-catalyzed tosyl group transfer reaction of p- methylphenylimide

Scheme 12. Desulfonation of p-toluenesulfonyl imines catalyzed by NHC

Scheme 13. Synthesis of axial chiral benzonitrile catalyzed by NHC

Scheme 14. Synthesis of nitriles by dehydration of primary amide and methylsilane catalyzed by aNHC

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氮杂环卡宾催化合成氰基化合物的研究进展

Recent Advances in the Synthesis of Cyanides Enabled by N-Heterocyclic Carbene Catalysis

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