氮杂环卡宾催化合成氰基化合物的研究进展

doi:10.6023/cjoc202303002

有机化学 ›› 2023, Vol. 43 ›› Issue (9): 3135-3145.DOI: 10.6023/cjoc202303002 上一篇下一篇

综述与进展

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)

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摘要/Abstract

氰基化合物不仅广泛存在于医药和农药分子中, 还是一类重要的中间体. 传统合成氰基化合物的方法是使用氰化钠、氰化钾和氢氰酸等最简单的氰化试剂, 但这类氰化试剂的剧毒性和不稳定性限制了其在合成中的应用. 因此发展有机氰化试剂和无氰源试剂构建氰基化合物的策略备受关注. 氮杂环卡宾是一类高效的有机小分子催化剂, 可用于实现多种碳-碳(C—C)和碳-杂(C—X)键的形成. 综述了氮杂环卡宾催化有机氰化试剂和无氰源试剂构建氰基化合物的反应, 目的是引起更多的化学工作者关注该领域的发展, 并提供氮杂环卡宾催化活化模式的新思路.

关键词: 氮杂环卡宾, 有机氰化试剂, 无氰源试剂, 氰化反应, 氰基化合物

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

引用此文

蔡远林, 吕亚, 聂桂花, 金智超, 池永贵. 氮杂环卡宾催化合成氰基化合物的研究进展[J]. 有机化学, 2023, 43(9): 3135-3145.

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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图/表 15

图1. 含氰基官能团的药物和农药分子

Figure 1. Drugs and pesticides containing cyano functional groups

图式1. 氮杂环卡宾催化活化TMSCN与醛的氰化反应

Scheme 1. Cyanidation of TMSCN with aldehydes catalyzed by NHC

图式2. 氮杂环卡宾不对称催化活化TMSCN与醛的氰化反应

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

图式3. 氮杂环卡宾活化氰基三甲基硅烷与醛或酮化合物的氰基化反应

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

图式4. 氮杂环卡宾催化醛、酮和亚胺的高效硅氰化反应

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

图式5. 氮杂环卡宾催化活化TMSCN与醛亚胺氰化反应的机理研究

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

图式6. 氮杂环卡宾催化TMSCN与对醌甲基类化合物的1,6-共轭加成反应

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

图式7. 氮杂环卡宾催化羰基化合物与氰甲酸乙酯和乙酰氰化物的氰化反应

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

图式8. 氮杂环卡宾催化α-酮酯的氰化反应

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

图式9. 氮杂环卡宾催化醛亚胺的氰化反应

Scheme 9. NHC-catalyzed cyanidation of aldimines

图式10. 氮杂环卡宾催化活化氰基膦酸二乙酯与羰基化合物的氰化反应

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

图式11. 氮杂环卡宾催化对甲苯磺亚胺的磺酰基转移反应

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

图式12. 氮杂环卡宾催化对甲苯磺酰亚胺脱磺酰化反应

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

图式13. 氮杂环卡宾催化轴手性苯腈的合成

Scheme 13. Synthesis of axial chiral benzonitrile catalyzed by NHC

图式14. 非传统氮杂环卡宾催化伯酰胺与甲硅烷脱水合成腈类化合物

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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