乙烯基重氮化合物非金属卡宾机制参与的反应

doi:10.6023/cjoc202401018

摘要/Abstract

乙烯基重氮化合物是一类重要的重氮化合物. 作为重氮化合物, 乙烯基重氮化合物生成的金属卡宾物种能发生插入反应、环加成等反应; 作为一类较弱的亲核试剂, 乙烯基重氮化合物不经过金属卡宾中间体与贫电子体系或自由基发生的反应最近几年受到关注. 乙烯基重氮化合物经过金属卡宾中间体的反应研究较为系统, 这方面的综述较多, 而乙烯基重氮化合物非金属卡宾路线参与的反应相对较为分散, 迄今还没有系统的讨论. 对乙烯基重氮化合物非金属卡宾机制参与的反应进行了综述, 并对该领域的发展方向进行了展望.

关键词: 乙烯基重氮化合物, 非金属卡宾机制, 环加成反应, 自由基反应

Vinyl diazo compounds are important compounds in organic synthesis. The generated vinyl metallic carbene species undergo insertion reactions, cycloaddition, and other reactions. As a class of weak nucleophiles, the reaction of vinyl diazo compounds with electron-deficient systems or free radicals not via metallic carbene intermediates has attracted attention from chemical societies in recent years. Carbene chemistry has been well investigated and reviewed. While the reactions of vinyl diazo compounds involved in the non-metallic carbene route are relatively scattered. Non-metallic carbene pathway transformations over the past two decades of vinyl diazo compounds are reviewed. Furthermore, the prospect in this field is also discussed.

Key words: vinyl diazo compounds, non metal carbene mechanism, cycloaddition, radical reaction

引用此文

蒋镓西, 刘全忠. 乙烯基重氮化合物非金属卡宾机制参与的反应[J]. 有机化学, 2024, 44(9): 2640-2657.

Jia-Xi Jiang, Quan-Zhong Liu. Non-Metallic Carbene Pathway Transformations of Vinyl Diazo Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2640-2657.

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图/表 36

图式1. 重氮化合物的化学性质

Scheme 1. Reactivity profile of diazo compounds

图式2. 乙烯基重氮化合物的制备

Scheme 2. Preparation of vinyl diazo compounds

图式3. Br?nsted酸催化乙烯基重氮化合物与富电子芳烃的Friedel-Crafts烷基化反应

Scheme 3. Br?nsted acid catalysed Friedel-Crafts alkylation of vinyl diazo compounds with electron enriched arenes

图式4. 乙烯基重氮化合物的氧化重排生成

Scheme 4. Oxidative rearrangement of vinyl diazo compounds

图式5. 乙烯基重氮化合物与亚硝酸叔丁酯的成环反应

Scheme 5. Cyclization of vinyl diazoacetates and tert-butyl nitrite

图式6. 乙烯基重氮化合物与原位生成的铜卡宾中间体的环加成反应

Scheme 6. Cycloaddition of vinyl diazo compounds and in situ formed copper-carbene

图式7. 铜催化乙烯基重氮化合物的不对称环加成反应

Scheme 7. Copper catalysed enantioselective cycloaddition of vinyl diazo compounds

图式8. 乙烯基重氮化合物对金属铜-氮宾的捕获

Scheme 8. Capture of metallic nitrene with vinyl diazo compounds

图式9. 乙烯基重氮化合物对锌-卡宾的环加成反应

Scheme 9. Cycloaddition of zinc carbene with vinyl diazo compounds

图式10. 钪催化烯醇硅醚重氮化合物与醛的Mukaiyama- Aldol反应

Scheme 10. Scandium catalysed Mukaiyama-Aldol reaction of silyl enolate diazo compounds with aldehydes

图式11. 金催化乙烯基重氮化合物与缩醛的反应

Scheme 11. Gold catalysed reaction of vinyl diazo compounds with acetals

图式12. 三氟甲烷磺酸催化芳香胺与乙烯基重氮化合物的Poparov重排反应[L=P(tBu)2(o-biphenyl)]

Scheme 12. TfOH catalysed Poparov rearrangement of arylimines and vinyl diazo compounds [L=P(tBu)2(o-biphenyl)]

图式13. 金催化喹啉氮氧化合物与乙烯基重氮化合物的反应

Scheme 13. Gold catalyzed reaction quinoline N-oxides with vinyl diazo compounds

图式14. Lewis酸催化烯醇重氮化合物与烯酮的加成

Scheme 14. Lewis acid catalysed addition of enol diazo compounds with enones

图式15. TBSOTf催化乙烯基重氮化合物与烯酮的Mukaiyama-aldol reaction反应

Scheme 15. TBSOTf catalysed Mukaiyama-aldol reaction of vinyl diazo compounds with enones

图式16. 三氟甲烷磺酸锌催化烯醇硅醚重氮化合物与烯酮的Mukaiyama-共轭反应

Scheme 16. Zinc triflate catalysed Mukaiyama-conjugate reaction of silyl enolate diazo compounds with enones

图式17. 醌氧正离子、醌亚胺缩酮和Eschenmoser盐的反应

Scheme 17. Reactions of vinyl diazo compounds with quinone oxonium ions, quinone imine ketals, and Eschenmoser’s salt

图式18. 金催化乙烯基重氮化合物与原位生成硝酮的[3＋2]环加成反应

Scheme 18. Gold catalysed [3＋2] cycloaddition of in situ formed nitrones with vinyl diazo compounds

图式19. B(C6F5)3催化乙烯基重氮化合物与硝酮的非对映选择性反应

Scheme 19. B(C6F5)3?catalysed diastereoselective reactions of vinyl diazo esters with nitrones

图式20. 金催化乙烯基重氮化合物与2-乙炔基苯甲醛的环化反应

Scheme 20. Gold catalysed annulations of 2-alkynylbenzaldehydes with vinyl diazo compounds

图式21. 金催化乙烯基重氮化合物2-乙炔基苯甲醛的[4＋2]环加成/重排反应

Scheme 21. Gold catalysed [4＋2] cycloaddition/re-arrangement of vinyl diazo compunds with 2-alkynyl benzaldehyde

图式22. Br?nsted acid催化乙烯基重氮化合物与1H-异苯并吡喃缩醛的反应

Scheme 22. Br?nsted acid catalysed reaction of 1H-isochromene acetals with vinyl diazo compounds

图式23. 金催化乙烯基重氮芳基酮与邻乙炔基苯甲醛亚胺的反应

Scheme 23. Gold(I)-catalysed reactions between N?(o?alkynylphenyl)imines and vinyl diazo aryl ketones

图式24. 乙烯基重氮酮与烯炔酮化合物成环反应

Scheme 24. Gold catalysed reactions between enynones and vinyl diazo ketones

图式25. 三氟甲烷磺酸钪催化乙烯基重氮化合物与3-磺酰吲哚的成环反应

Scheme 25. Sc(OTf)3 catalyzed annulation of vinyl diazo compound with 3-sulphonyl indoles

图式26. 乙烯基重氮化合物与苯并呋喃衍生的氮杂二烯的反电子需求的氮杂D-A反应

Scheme 26. Inverse-electron-demand aza-Diels-Alder reaction of vinyl diazo compound and benzofuran-derived azadienes

图式27. 光促进乙烯基重氮化合物与全氟碘代烷的1,3-自由基加成反应

Scheme 27. Light promoted radical 1,3-addition of perfluoroalkyl iodides to vinyl-diazoacetates

图式28. 光促进乙烯基重氮化合物的自由基1,3-硒磺酰化反应

Scheme 28. Light-driven radical 1,3-selenosulfonylation of vinyl diazo compounds

图式29. 光催化乙烯基重氮化合物与富电子烯烃的自由基环加成反应

Scheme 29. Light catalysed radical cyclization of vinyl diazo compounds with electron enriched olefins

图式30. 铁催化乙烯基重氮化合物与富电子烯烃的环加成反应

Scheme 30. Iron catalyzed cycloaddition of vinyl diazo compound with electron enriched alkenes

图式31. 可见光促进乙烯基重氮化合物与N-芳基氯代二氟甲基炔基酮亚胺的自由基串联成环反应

Scheme 31. Visible-light-promoted radical tandem cyclization of N-aryl chloro difluoromethyl alkynyl ketoimines with vinyl diazo compounds

图式32. 可见光促进乙烯基重氮化合物与溴代二氟甲基炔基酮的自由基串联成环反应

Scheme 32. Visible-light-promoted radical tandem cyclization of bromo difluoromethyl alkynyl ketones with vinyl diazo compounds

图式33. 光催化乙烯基重氮化合物与吲哚的[3＋2]环加成反应

Scheme 33. Photocatalysed [3＋2] cycloaddition between indoles with vinyl diazo compounds

图式34. 光催化乙烯基重氮化合物的自身[3＋2]环加成反应

Scheme 34. Photocatalytic self [3＋2] cycloaddition of vinyl diazo compounds

图式35. 光催化乙烯基重氮化合物与二环[1,1,0]丁烷的烯反应

Scheme 35. Photocatalytic ene reaction of vinyl diazo compounds with bicyclo[1,1,0] butanes

图式36. 光催化氮杂环卡宾硼烷络合物与乙烯基重氮化合物的自由基环化反应

Scheme 36. Photocatalytic radical cyclization of N-heterocyclic carbene-borane complexes with vinyl diazo compounds

参考文献 42

[1]	(a) Michael, P. D.; Doyle, M. P. In Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, Hoboken, Newjersy, U. S. A., Wiley, 1998. pmid: 30543264
	(b) Suleman, M.; Lu, P.; Wang, Y. Org. Chem. Front. 2021, 8, 2059. pmid: 30543264
	(c) Akter, M.; Rupa, K.; Anbarasan, P. Chem. Rev. 2022, 122, 13108. pmid: 30543264
	(d) Ciszewski, Ł. W.; Rybicka-Jasińska, K.; Gryko, D. Org. Biomol. Chem. 2019, 17, 432. doi: 10.1039/c8ob02703j pmid: 30543264
	(e) Zhu, D.; Chen, L.; Fan, H.; Yao, Q.; Zhu, S. Chem. Soc. Rev. 2020, 49, 908. pmid: 30543264
	(f) Candeias, N. R.; Paterna, R.; Gois, P. M. P. Chem. Rev. 2016, 116, 293. pmid: 30543264
	(g) Ford, A.; Miel, H.; Ring, A.; Slattery, C. N.; Maguire, A. R.; McKervey, M. A. Chem. Rev. 2015, 115, 9981. pmid: 30543264
	(h) Qiu, D.; Wang, J. In Recent Developments of Diazo Compounds in Organic Synthesis, World Scientific (Europe), Singapore, 2020. pmid: 30543264
	(i) Tian, M.; Yang, L.; Liu, B.; Chang, J. Chin. J. Chem. 2023, 41, 1327. pmid: 30543264
[2]	(a) Zhang, Y.; Zhou, G.; Gong, X.; Guo, Z.; Qi, X.; Shen, X. Angew. Chem., Int. Ed. 2022, 61, e202202175.
	(b) Roy, A.; Goswami, S. P.; Sarker, A. Synth. Commun. 2018, 48, 2003.
	(c) Wu, W.; Lin, Z.; Jiang, H. Org. Biomol. Chem., 2018, 16, 7315.
	(d) Dong, K.; Liu, M.; Xu, X. Molecules 2022, 27, 3088.
	(e) Hao, T.; Shi, M.; Wei, Y. Chin. J. Chem. 2023, 41, 301.
[3]	(a) Che, J.; Niu, L.; Xiong, D.; Hu, W. Nat. Commun. 2020, 11, 1511. pmid: 26847664
	(b) Guo, X.; Hu, W. Acc. Chem. Res. 2013, 46, 2427. pmid: 26847664
	(c) Zhang, D.; Hu, W. Chem. Rec. 2017, 17, 739. pmid: 26847664
	(d) Xia, Y.; Qiu, D.; Wang, J. Chem. Rev. 2017, 117, 13810. pmid: 26847664
	(e) Qiu, H.; Li, M.; Jiang, L.-Q.; Lv, F.-P.; Zhan, L.; Zhai, C.-W.; Doyle, M. P.; Hu, W.-H. Nat. Chem. 2012, 4, 733. pmid: 26847664
	(f) Zhou, C.-Y.; Wang, J.-C.; Wei, J.; Xu, Z.-J.; Guo, Z.; Low, K.-H.; Che, C.-M. Angew. Chem., Int. Ed. 2012, 51, 11376. pmid: 26847664
	(g) Jia, S.; Xing, D.; Zhang, D.; Hu, W. Angew. Chem., Int. Ed. 2014, 53, 13098. pmid: 26847664
	(h) Nicolle, S. M.; Lewis, W.; Hayes, C. J.; Moody, C. J. Angew. Chem., Int. Ed. 2016, 55, 3749. doi: 10.1002/anie.201511433 pmid: 26847664
	(i) Yuan, W.; Eriksson, L.; Szabό, K. J. Angew. Chem., Int. Ed. 2016, 55, 8410. pmid: 26847664
[4]	(a) Tang, F.; Pu, M. J. Am. Chem. Soc. 2021, 143, 2394. pmid: 21553888
	(b) Tan, F.; Liu, X.; Wang, Y.; Dong, S.; Yu, H.; Feng, X. Angew. Chem., Int. Ed. 2018, 57, 16176. pmid: 21553888
	(c) Xia, A.-J.; Kang, T.-R.; He, L.; Chen, L.-M.; Li, W.-T.; Yang, J.-L.; Liu, Q.-Z. Angew. Chem., Int. Ed. 2016, 55, 1441. doi: 10.1002/anie.201508804 pmid: 21553888
	(d) Li, S.-S.; Sun, S.; Wang, J.-B. Angew. Chem., Int. Ed. 2021, 61, e202115098. pmid: 21553888
	(e) Li, W.; Wang, J.; Hu, X. L.; Shen, K.; Wang, W. T.; Chu, Y. Y.; Lin, L. L.; Liu, X. H.; Feng, X. M. J. Am. Chem. Soc. 2010, 132, 8532. pmid: 21553888
	(f) Gao, L.; Kang, B. C.; Hwang, G.-S.; Ryu, D. H. Angew. Chem., Int. Ed. 2012, 51, 8322. pmid: 21553888
	(g) Hashimoto, T.; Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2011, 133, 8834. doi: 10.1021/ja202070j pmid: 21553888
[5]	(a) Chen, Y.; Yu, R.; Wang, M.; Huang, Y.; Peng, Y. Adv. Synth. Catal. 2021, 363, 4856.
	(b) Du, F.; Yin, L.; Ning, Y.; Peng, Y. Adv. Synth. Catal. 2016, 358, 2280.
	(c) B. M. Trost, B. M.; Malhotra, S.; Koschker, P.; Ellerbrock, P. J. Am. Chem. Soc. 2012, 134, 2075.
	(d) Trost, B. M.; Malhotra, S.; Fred, B. A. J. Am. Chem. Soc. 2009, 131, 1674.
	(e) Wang, F.; Liu, X.; Zhang, Y.; Lin, L.; Feng, X. Chem. Commun. 2009, 7297.
	(f) Trost, B. M.; Malhotra, S.; Koschker, P.; Ellerbrock, P. J. Am. Chem. Soc. 2011, 134, 2075.
	(g) Trost, B. M.; Malhotra, S.; Ellerbrock, P. Org. Lett. 2013, 15, 440.
[6]	(a) Davies, H. M. L.; Saikali, E.; Clark, T. J.; Chee, E. H. Tetrahedron Lett. 1990, 31, 6299.
	(b) Davies, H. M. L.; Clark, T. J.; Smith, H. D. J. Org. Chem. 1991, 56, 3817.
[7]	Davies, H. M. L.; Hougland, P. W.; Cantrell, W. R. Synth. Commmun. 1992, 22, 971.
[8]	(a) Cheng, Q.-Q.; Yu, Y.; Yedoyan, J.; Doyle, M. P. ChemCatChem 2018, 10, 488.
	(b) López, E.; González-Pelayo, S.; López, L. A. Chem. Rec. 2017, 17, 312.
	(c) Marichev, K. O.; Zheng, H.; Doyle, M. P. In Transition Metal Catalysed Carbene Transformations, Wiley‐VCH GmbH, Weinheim Germany, 2022, Chapter 5, pp. 139-168, https://doi.org/10.1002/9783527829170.
	(d) Cheng, Q.-Q.; Deng, Y.; Lankelma, M.; Doyle, M. P. Chem. Soc. Rev. 2017, 46, 5425.
	(e) Xu, X.; Doyle, M. P. Acc. Chem. Res. 2014, 47, 1396.
	(f) Bao, M.; Zhou, S.; Xu, X. In More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles, John Wiley & Sons, New York, U. S. A., 2022, https://doi.org/10.1002/9781119757153.
[9]	Zheng, H.; Dong, K.; Wherritt, D.; Arman, H.; Doyle, M. P. Angew. Chem., Int. Ed. 2020, 59, 13613.
[10]	Barluenga, J.; Lonzi, G.; Riesgo, L.; Tomás, M.; López, L. A. J. Am. Chem. Soc. 2011, 133, 18138. doi: 10.1021/ja208965b pmid: 22004455
[11]	Angelis, L. A.; Zheng, H.; Perz, M. T.; Arman, H.; Doyle, M. P. Org. Lett. 2021, 23, 6542. doi: 10.1021/acs.orglett.1c02352 pmid: 34370472
[12]	Barluenga, J.; Riesgo, L.; López, L. A.; Rubio, E.; Tomás, M. Angew. Chem., Int. Ed. 2009, 48, 7569. doi: 10.1002/anie.200903902 pmid: 19739180
[13]	Xu, Y.; Wang, Z.; Sun, J. Org. Lett. 2021, 23, 7613.
[14]	Barluenga, J.; Riesgo, L.; Lonzi, G.; Tomás, M.; López, L. A. Chem.-Eur. J. 2012, 18, 9221. doi: 10.1002/chem.201200998 pmid: 22730267
[15]	Mata, S.; González, M. J.; López, L. A.; Vicente, R. Chem.-Eur. J. 2017, 23, 1013.
[16]	Doyle, M. P.; Kundu, K.; Russell, A. E. Org. Lett. 2005, 7, 5171.
[17]	Pagar, V. V.; Jadhav, A. M.; Liu, R.-S. J. Org. Chem. 2013, 78, 5711.
[18]	Jadhav, A. M.; Pagar, V. V.; Liu, R.-S. Angew. Chem., Int. Ed. 2012, 51, 11809.
[19]	Pagar, V. V.; Liu, R.-S. Org. Biomol. Chem. 2015, 13, 6166.
[20]	Deng, G.; Tian, X.; Qu, Z.; Wang, J. Angew. Chem., Int. Ed. 2002, 41, 2773.
[21]	Bel, M. D.; Rovira, A.; Guerrero, C. A. J. Am. Chen. Soc. 2013, 135, 12188.
[22]	Liu, Y.; Zhang, Y.; Jee, N.; Doyle, M. P. Org. Lett. 2008, 10, 1605. doi: 10.1021/ol800298n pmid: 18351770
[23]	Zheng, H.; Wang, K.; Faghihi, S.; Griffith, W. P.; Arman, H.; Doyle, M. P. ACS Catal. 2021, 11, 9869.
[24]	Pagar, V. V.; Liu, R. S. Angew. Chem., Int. Ed. 2015, 54, 4923.
[25]	Stefkova, K.; Guerzoni, M. G.; van Ingen, Y.; Richard, E.; Melen, R. L. Org. Lett. 2023, 25, 500.
[26]	Raj, A. S. K.; Liu, R.-S. Angew. Chem., Int. Ed. 2019, 58, 10980.
[27]	Raj, A. S. K.; Liu, R.-S. Adv. Synth. Catal. 2020, 362, 2517.
[28]	Zheng, H.; Wang, K.; Angelis, L. D.; Arman, H. D.; Doyle, M. P. J. Am. Chem. Soc. 2021, 143, 15391.
[29]	Raj, A. S. K.; Narode, A. S.; Liu, R.-S. Org. Lett. 2021, 23, 1378.
[30]	Kardile, R. D.; Liu, R.-S. Org. Lett. 2020, 22, 8229.
[31]	Jiang, Q.; Yang, T.; Li, Q.; Liang, G.-M.; Liu, Y.; He, C.-Y.; Chu, W.-D.; Liu, Q.-Z. Org. Lett. 2023, 25, 3184. doi: 10.1021/acs.orglett.3c00192 pmid: 37125696
[32]	Yang, T.; Jiang, Q.; Wang, C.-M.; Li, S.-L.; He, C.-Y.; Chu, W.-D.; Liu, Q.-Z. Org. Lett. 2023, 25, 2243.
[33]	Li, W.; Zhou, X.; Xiao, T.; Ke, Z.; Zhou, L. CCS Chem. 2022, 4, 638.
[34]	Li, W.; Zhou, L. Green. Chem. 2021, 23, 6652.
[35]	Sarabia, F. J.; Li, Q.; Ferreira, E. M. Angew. Chem., Int. Ed. 2018, 57, 11015.
[36]	Cho, Y. H.; Kim, J. H.; An, H.; Ahn, K.-H.; Kang, E. J. Adv. Synth. Catal. 2020, 362. 2183.
[37]	Li, W.; Zhou, L. Org. Lett. 2021, 23, 4279.
[38]	Li, S.; Zhou, L. Org. Lett. 2023, 25, 8700.
[39]	Gall, B. K.; Smith, A. K.; Ferreira, E. M. Angew. Chem., Int. Ed. 2022, 61, e202212187.
[40]	Li, W.; Li, S.; Empel, C.; Koenigs, R. M.; Zhou, L. Angew. Chem., Int. Ed. 2023, 62, e202309947.
[41]	Dasgupta, A.; Bhattacharjee, S.; Tong, Z.; Guin, A.; McNamee, R. E.; Christensen, K. E.; Biju, A. T.; Anderson, E. A. J. Am. Chem. Soc. 2024, 146, 1196. doi: 10.1021/jacs.3c13080 pmid: 38157245
[42]	Xie, Y.; Zhang, R.; Chen, Z.-L.; Rong, M.; He, R.; Ni, S.; He, X.-K.; Xiao, W.-J.; Xuan, J. Adv. Sci. 2024, 11, 2306728.