REVIEWS

Non-Metallic Carbene Pathway Transformations of Vinyl Diazo Compounds

  • Jia-Xi Jiang ,
  • Quan-Zhong Liu
Expand
  • Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong, Sichuan 637002

Received date: 2024-03-02

  Revised date: 2024-05-05

  Online published: 2024-05-11

Supported by

National Natural Science Foundation of China(21572183)

Abstract

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.

Cite this article

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 . DOI: 10.6023/cjoc202401018

References

[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.
[1]
(b) Suleman, M.; Lu, P.; Wang, Y. Org. Chem. Front. 2021, 8, 2059.
[1]
(c) Akter, M.; Rupa, K.; Anbarasan, P. Chem. Rev. 2022, 122, 13108.
[1]
(d) Ciszewski, ?. W.; Rybicka-Jasińska, K.; Gryko, D. Org. Biomol. Chem. 2019, 17, 432.
[1]
(e) Zhu, D.; Chen, L.; Fan, H.; Yao, Q.; Zhu, S. Chem. Soc. Rev. 2020, 49, 908.
[1]
(f) Candeias, N. R.; Paterna, R.; Gois, P. M. P. Chem. Rev. 2016, 116, 293.
[1]
(g) Ford, A.; Miel, H.; Ring, A.; Slattery, C. N.; Maguire, A. R.; McKervey, M. A. Chem. Rev. 2015, 115, 9981.
[1]
(h) Qiu, D.; Wang, J. In Recent Developments of Diazo Compounds in Organic Synthesis, World Scientific (Europe), Singapore, 2020.
[1]
(i) Tian, M.; Yang, L.; Liu, B.; Chang, J. Chin. J. Chem. 2023, 41, 1327.
[2]
(a) Zhang, Y.; Zhou, G.; Gong, X.; Guo, Z.; Qi, X.; Shen, X. Angew. Chem., Int. Ed. 2022, 61, e202202175.
[2]
(b) Roy, A.; Goswami, S. P.; Sarker, A. Synth. Commun. 2018, 48, 2003.
[2]
(c) Wu, W.; Lin, Z.; Jiang, H. Org. Biomol. Chem., 2018, 16, 7315.
[2]
(d) Dong, K.; Liu, M.; Xu, X. Molecules 2022, 27, 3088.
[2]
(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.
[3]
(b) Guo, X.; Hu, W. Acc. Chem. Res. 2013, 46, 2427.
[3]
(c) Zhang, D.; Hu, W. Chem. Rec. 2017, 17, 739.
[3]
(d) Xia, Y.; Qiu, D.; Wang, J. Chem. Rev. 2017, 117, 13810.
[3]
(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.
[3]
(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.
[3]
(g) Jia, S.; Xing, D.; Zhang, D.; Hu, W. Angew. Chem., Int. Ed. 2014, 53, 13098.
[3]
(h) Nicolle, S. M.; Lewis, W.; Hayes, C. J.; Moody, C. J. Angew. Chem., Int. Ed. 2016, 55, 3749.
[3]
(i) Yuan, W.; Eriksson, L.; Szab?, K. J. Angew. Chem., Int. Ed. 2016, 55, 8410.
[4]
(a) Tang, F.; Pu, M. J. Am. Chem. Soc. 2021, 143, 2394.
[4]
(b) Tan, F.; Liu, X.; Wang, Y.; Dong, S.; Yu, H.; Feng, X. Angew. Chem., Int. Ed. 2018, 57, 16176.
[4]
(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.
[4]
(d) Li, S.-S.; Sun, S.; Wang, J.-B. Angew. Chem., Int. Ed. 2021, 61, e202115098.
[4]
(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.
[4]
(f) Gao, L.; Kang, B. C.; Hwang, G.-S.; Ryu, D. H. Angew. Chem., Int. Ed. 2012, 51, 8322.
[4]
(g) Hashimoto, T.; Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2011, 133, 8834.
[5]
(a) Chen, Y.; Yu, R.; Wang, M.; Huang, Y.; Peng, Y. Adv. Synth. Catal. 2021, 363, 4856.
[5]
(b) Du, F.; Yin, L.; Ning, Y.; Peng, Y. Adv. Synth. Catal. 2016, 358, 2280.
[5]
(c) B. M. Trost, B. M.; Malhotra, S.; Koschker, P.; Ellerbrock, P. J. Am. Chem. Soc. 2012, 134, 2075.
[5]
(d) Trost, B. M.; Malhotra, S.; Fred, B. A. J. Am. Chem. Soc. 2009, 131, 1674.
[5]
(e) Wang, F.; Liu, X.; Zhang, Y.; Lin, L.; Feng, X. Chem. Commun. 2009, 7297.
[5]
(f) Trost, B. M.; Malhotra, S.; Koschker, P.; Ellerbrock, P. J. Am. Chem. Soc. 2011, 134, 2075.
[5]
(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.
[6]
(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.
[8]
(b) López, E.; González-Pelayo, S.; López, L. A. Chem. Rec. 2017, 17, 312.
[8]
(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.
[8]
(d) Cheng, Q.-Q.; Deng, Y.; Lankelma, M.; Doyle, M. P. Chem. Soc. Rev. 2017, 46, 5425.
[8]
(e) Xu, X.; Doyle, M. P. Acc. Chem. Res. 2014, 47, 1396.
[8]
(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.
[11]
Angelis, L. A.; Zheng, H.; Perz, M. T.; Arman, H.; Doyle, M. P. Org. Lett. 2021, 23, 6542.
[12]
Barluenga, J.; Riesgo, L.; López, L. A.; Rubio, E.; Tomás, M. Angew. Chem., Int. Ed. 2009, 48, 7569.
[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.
[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.
[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.
[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.
[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.
Outlines

/

〈 〉