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Palladium-Catalyzed Denitrative Mizoroki–Heck Reactions of Aryl or Alkyl Olefins with Nitrobenzenes

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Abstract

Palladium-catalyzed Mizoroki–Heck reactions of monosubstituted olefins with nitrobenzenes via C–NO2 bond activation has been reported. In these transformations, the combination of Pd(acac)2 and Brettphos as ligand was chosen as the best catalytic system, CsF was proved to be the best base, and cyclohexane was the best solvent. More importantly, 7–9 equiv of nitrobenzene were necessary for this reaction to achieve excellent yields. Styrenes and nitrobenzenes with various substituents can well be used in these processes, and a variety of (E)-1,2-diarylethylene derivatives were synthesized.

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REFERENCES

  1. Chuang, C.-Y., Ho, Y.-C., Lin, C.-W., Yang, W.-E., Yu, Y.-L., Tsai, M.-C., Yang, S.-F., and Su, S.-C., J. Ethnopharmacol., 2020, vol. 252, article ID 112601. https://doi.org/10.1016/j.jep.2020.112601

  2. Eräsalo, H., Hämäläinen, M., Leppänen, T., MäkiOpas, I., Laavola, M., Haavikko, R., Yli-Kauhalu­oma, J., and Moilanen, E., J. Nat. Prod., 2018, vol. 81, p. 1131. https://doi.org/10.1021/acs.jnatprod.7b00384

    Article  CAS  Google Scholar 

  3. Harmalkar, D.S., Lu, Q., and Lee, K., J. Nat. Prod., 2018, vol. 81, p. 798. https://doi.org/10.1021/acs.jnatprod.7b00865

    Article  CAS  Google Scholar 

  4. Kolodziejczyk-Czepas, J. and Czepas, J., Phytochem. Rev., 2019, vol. 18, p. 1375. https://doi.org/10.1007/s11101-019-09652-w

    Article  CAS  Google Scholar 

  5. Péresse, T., Jézéquel, G., Allard, P.-M., Pham, V.-C., Huong, D.T.M., Blanchard, F., Bignon, J., Lévaique, H., Wolfender, J.-L., Litaudon, M., and Roussi, F., J. Nat. Prod., 2017, vol. 80, p. 2684. https://doi.org/10.1021/acs.jnatprod.7b00409

    Article  CAS  Google Scholar 

  6. Shi, X., Sun, R., Zhao, Y., Fu, R., Wang, R., Zhao, H., Wang, Z., Tang, F., Zhang, N., Tian, X., and Yao, J., RSC Adv., 2018, vol. 8, p. 20411. https://doi.org/10.1039/C8RA00798E

    Article  CAS  Google Scholar 

  7. Stockdale, D.P., Titunick, M.B., Biegler, J.M., Reed, J.L., Hartung, A.M., Wiemer, D.F., Mc­Laughlin, P.J., and Neighbors, J.D., Bioorg. Med. Chem., 2017, vol. 25, p. 4464. https://doi.org/10.1016/j.bmc.2017.06.035

    Article  CAS  Google Scholar 

  8. Sui, X., Weitz, A.C., Farquhar, E.R., Badiee, M., Banerjee, S., von Lintig, J., Tochtrop, G.P., Pal­czewski, K., Hendrich, M.P., and Kiser, P.D., Biochemistry, 2017, vol. 56, p. 2836. https://doi.org/10.1021/acs.biochem.7b00251

    Article  CAS  Google Scholar 

  9. Sun, Y., Liang, X., Cheng, H., Wang, W., Jiang, X., He, P., Zhao, Y., and Wu, J., Mini-Rev. Org. Chem., 2017, vol. 14, p. 24. https://doi.org/10.2174/1570193X13666161102152403

    Article  CAS  Google Scholar 

  10. Tang, X.-L., Yan, L., Zhu, L., Jiao, D.-M., Chen, J., and Chen, Q.-Y., J. Pharmacol. Sci., 2017, vol. 135, p. 1. https://doi.org/10.1016/j.jphs.2017.06.006

    Article  CAS  Google Scholar 

  11. Mizoroki, T., Mori, K., and Ozaki, A., Bull. Chem. Soc. Jpn., 1971, vol. 44, p. 581. https://doi.org/10.1246/bcsj.44.581

    Article  CAS  Google Scholar 

  12. Heck, R.F. and Nolley, J.P., J. Org. Chem., 1972, vol. 37, p. 2320. https://doi.org/10.1021/jo00979a024

    Article  CAS  Google Scholar 

  13. Heck, R.F., Acc. Chem. Res., 1979, vol. 12, p. 146. https://doi.org/10.1021/ar50136a006

    Article  CAS  Google Scholar 

  14. Heck, R.F., Org. React., 1982, vol. 27, p. 345. https://doi.org/10.1002/0471264180.or027.02

    Article  CAS  Google Scholar 

  15. Beletskaya, I.P. and Cheprakov, A.V., Chem. Rev., 2000, vol. 100, p. 3009. https://doi.org/10.1021/cr9903048

    Article  CAS  Google Scholar 

  16. Cabri, W. and Candiani, I., Acc. Chem. Res., 1995, vol. 28, p. 2. https://doi.org/10.1021/ar00049a001

    Article  CAS  Google Scholar 

  17. Christoffel, F. and Ward, T.R., Catal. Lett., 2018, vol. 148, p. 489. https://doi.org/10.1007/s10562-017-2285-0

    Article  CAS  Google Scholar 

  18. Crisp, G.T., Chem. Soc. Rev., 1998, vol. 27, p. 427. https://doi.org/10.1039/A827427Z

    Article  CAS  Google Scholar 

  19. Dounay, A.B. and Overman, L.E., Chem. Rev., 2003, vol. 103, p. 2945. https://doi.org/10.1021/cr020039h

    Article  CAS  Google Scholar 

  20. Jagtap, S., Catalysts, 2017, vol. 7, article no. 267. https://doi.org/10.3390/catal7090267

  21. Nakashima, Y., Hirata, G., Sheppard, T.D., and Nishi­kata, T., Asian J. Org. Chem., 2020, vol. 9, p. 480. https://doi.org/10.1002/ajoc.201900741

    Article  CAS  Google Scholar 

  22. Baruwati, B., Guin, D., and Manorama, S.V., Org. Lett., 2007, vol. 9, p. 5377. https://doi.org/10.1021/ol702064x

    Article  CAS  Google Scholar 

  23. Bharamanagowda, M.M. and Panchangam, R.K., Appl. Organomet. Chem., 2020, vol. 34, article ID e5837. https://doi.org/10.1002/aoc.5837

  24. Ghosh, K., Dhara, S., Jana, S., Das, S., and Roy, S., New J. Chem., 2019, vol. 43, p. 1993. https://doi.org/10.1039/C8NJ05118F

    Article  CAS  Google Scholar 

  25. Jerome, P., Babu, S.G., and Karvembu, R., Catal. Lett., 2021, vol. 151, p. 1633. https://doi.org/10.1007/s10562-020-03413-7

    Article  CAS  Google Scholar 

  26. Kandathil, V., Fahlman, B.D., Sasidhar, B.S., Patil, S.A., and Patil, S.A., New J. Chem., 2017, vol. 41, p. 9531. https://doi.org/10.1039/C7NJ01876B

    Article  CAS  Google Scholar 

  27. Kempasiddhaiah, M., Kandathil, V., Dateer, R.B., Sasidhar, B.S., Patil, S.A., and Patil, S.A., Appl. Organomet. Chem., 2019, vol. 33, article ID e4846. https://doi.org/10.1002/aoc.4846

  28. Mahmoudi, H., Valentini, F., Ferlin, F., Bivona, L.A., Anastasiou, I., Fusaro, L., Aprile, C., Marrocchi, A., and Vaccaro, L., Green Chem., 2019, vol. 21, p. 355. https://doi.org/10.1039/C8GC03228A

    Article  CAS  Google Scholar 

  29. Ocansey, E., Darkwa, J., and Makhubela, B.C.E., Polyhedron, 2019, vol. 166, p. 52. https://doi.org/10.1016/j.poly.2019.03.030

    Article  CAS  Google Scholar 

  30. Polshettiwar, V., Hesemann, P., and Moreau, J.J.E., Tetrahedron Lett., 2007, vol. 48, p. 5363. https://doi.org/10.1016/j.tetlet.2007.06.029

    Article  CAS  Google Scholar 

  31. Rago, A.J. and Dong, G., Org. Lett., 2020, vol. 22, p. 3770. https://doi.org/10.1021/acs.orglett.0c00952

    Article  CAS  Google Scholar 

  32. Santos, B.F., Silva, B.A.L., Oliveira, A.R., Sarra­giotto, M.H., Rinaldi, A.W., and Domingues, N.L.C., Synthesis, 2021, vol. 53, p. 1301. https://doi.org/10.1055/s-0040-1705938

    Article  CAS  Google Scholar 

  33. Sperger, T., Stirner, C.K., and Schoenebeck, F., Synthesis, 2017, vol. 49, p. 115. https://doi.org/10.1055/s-0036-1588318

    Article  CAS  Google Scholar 

  34. Modern Arylation Methods, Ackermann, L., Ed., Weinheim: Wiley-VCH, 2009. https://doi.org/10.1002/9783527627325

  35. Fañanás-Mastral, M., Synthesis, 2017, vol. 49, p. 1905. https://doi.org/10.1055/s-0036-1589483

    Article  CAS  Google Scholar 

  36. Jasch, H., Scheumann, J., and Heinrich, M.R., J. Org. Chem., 2012, vol. 77, p. 10699. https://doi.org/10.1021/jo301980j

    Article  CAS  Google Scholar 

  37. Kindt, S. and Heinrich, M.R., Synthesis, 2016, vol. 48, p. 1597. https://doi.org/10.1055/s-0035-1561586

    Article  CAS  Google Scholar 

  38. Ruch, J., Aubin, A., Erbland, G., Fortunato, A., and Goddard, J.-P., Chem. Commun., 2016, vol. 52, p. 2326. https://doi.org/10.1039/C5CC08927A

    Article  CAS  Google Scholar 

  39. Activation of Unreactive Bonds and Organic Synthesis, Murai, S., Ed., Berlin, Springer, 1999. https://doi.org/10.1007/3-540-68525-1

  40. Homogeneous Catalysis for Unreactive Bond Activation, Shi, Z.-J., Ed., Hoboken, NJ: Wiley, 2015. https://doi.org/10.1002/9781118788981

  41. Colby, D.A., Bergman, R.G., and Ellman, J.A., Chem. Rev., 2010, vol. 110, p. 624. https://doi.org/10.1021/cr900005n

    Article  CAS  Google Scholar 

  42. Davies, H.M.L., Du Bois, J., and Yu, J.-Q., Chem. Soc. Rev., 2011, vol. 40, p. 1855. https://doi.org/10.1039/C1CS90010B

    Article  CAS  Google Scholar 

  43. Sun, C.-L., Li, B.-J., and Shi, Z.-J., Chem. Rev., 2011, vol. 111, p. 1293. https://doi.org/10.1021/cr100198w

    Article  CAS  Google Scholar 

  44. Yu, D.-G., Li, B.-J., and Shi, Z.-J., Acc. Chem. Res., 2010, vol. 43, p. 1486. https://doi.org/10.1021/ar100082d

    Article  CAS  Google Scholar 

  45. Rosen, B.M., Quasdorf, K.W., Wilson, D.A., Zhang, N., Resmerita, A.-M., Garg, N.K., and Percec, V., Chem. Rev., 2011, vol. 111, p. 1346. https://doi.org/10.1021/cr100259t

    Article  CAS  Google Scholar 

  46. Cornella, J., Zarate, C., and Martin, R., Chem. Soc. Rev., 2014, vol. 43, p. 8081. https://doi.org/10.1039/C4CS00206G

    Article  CAS  Google Scholar 

  47. Wang, Q., Su, Y., Li, L., and Huang, H., Chem. Soc. Rev., 2016, vol. 45, p. 1257. https://doi.org/10.1039/C5CS00534E

    Article  CAS  Google Scholar 

  48. Boit, T.B., Bulger, A.S., Dander, J.E., and Garg, N.K., ACS Catal., 2020, vol. 10, p. 12109. https://doi.org/10.1021/acscatal.0c03334

    Article  CAS  Google Scholar 

  49. Jones, W.D., Nature, 1993, vol. 364, p. 676. https://doi.org/10.1038/364676a0

    Article  Google Scholar 

  50. Jun, C.-H., Chem. Soc. Rev., 2004, vol. 33, p. 610. https://doi.org/10.1039/B308864M

    Article  CAS  Google Scholar 

  51. Fumagalli, G., Stanton, G., and Bower, J.F., Chem. Rev., 2017, vol. 117, p. 9404. https://doi.org/10.1021/acs.chemrev.6b00599

    Article  CAS  Google Scholar 

  52. Amii, H. and Uneyama, K., Chem. Rev., 2009, vol. 109, p. 2119. https://doi.org/10.1021/cr800388c

    Article  CAS  Google Scholar 

  53. Braun, T. and Wehmeier, F., Eur. J. Inorg. Chem., 2011, vol. 2011, p. 613. https://doi.org/10.1002/ejic.201001184

    Article  CAS  Google Scholar 

  54. Ahrens, T., Kohlmann, J., Ahrens, M., and Braun, T., Chem. Rev., 2015, vol. 115, p. 931. https://doi.org/10.1021/cr500257c

    Article  CAS  Google Scholar 

  55. Ono, N., The Nitro Group in Organic Synthesis, New York: Wiley-VCH, 2001. https://doi.org/10.1002/0471224480

  56. Booth, G., Ullmann’s Encyclopedia of Industrial Chemistry, New York: Wiley-VCH, 2012.

  57. Yadav, M.R., Nagaoka, M., Kashihara, M., Zhong, R.-L., Miyazaki, T., Sakaki, S., and Nakao, Y., J. Am. Chem. Soc., 2017, vol. 139, p. 9423. https://doi.org/10.1021/jacs.7b03159

    Article  CAS  Google Scholar 

  58. Inoue, F., Kashihara, M., Yadav, M.R., and Nakao, Y., Angew. Chem., Int. Ed., 2017, vol. 56, p. 13307. https://doi.org/10.1002/anie.201706982

    Article  CAS  Google Scholar 

  59. Feng, B., Yang, Y., and You, J., Chem. Commun., 2020, vol. 56, p. 790. https://doi.org/10.1039/C9CC08663C

    Article  CAS  Google Scholar 

  60. Kashihara, M., Yadav, M.R., and Nakao, Y., Org. Lett., 2018, vol. 20, p. 1655. https://doi.org/10.1021/acs.orglett.8b00430

    Article  CAS  Google Scholar 

  61. Li, Z., Peng, Y., and Wu, T., Org. Lett., 2021, vol. 23, p. 881. https://doi.org/10.1021/acs.orglett.0c04104

    Article  CAS  Google Scholar 

  62. Feng, B., Yang, Y., and You, J., Chem. Sci., 2020, vol. 11, p. 6031. https://doi.org/10.1039/D0SC01641A

    Article  CAS  Google Scholar 

  63. Asahara, K.K., Okita, T., Saito, A.N., Muto, K., Nakao, Y., and Yamaguchi, J., Org. Lett., 2019, vol. 21, p. 4721. https://doi.org/10.1021/acs.orglett.9b01593

    Article  CAS  Google Scholar 

  64. Zhou, F., Zhou, F., Su, R., Yang, Y., and You, J., Chem. Sci., 2020, vol. 11, p. 7424. https://doi.org/10.1039/D0SC02058C

    Article  CAS  Google Scholar 

  65. Muto, K., Okita, T., and Yamaguchi, J., ACS Catal., 2020, vol. 10, p. 9856. https://doi.org/10.1021/acscatal.0c02990

    Article  CAS  Google Scholar 

  66. Okita, T., Asahara, K.K., Muto, K., and Yamaguchi, J., Org. Lett., 2020, vol. 22, p. 3205. https://doi.org/10.1021/acs.orglett.0c00983

    Article  CAS  Google Scholar 

  67. Aranyos, A., Old, D.W., Kiyomori, A., Wolfe, J.P., Sadighi, J.P., and Buchwald, S.L., J. Am. Chem. Soc., 1999, vol. 121, p. 4369. https://doi.org/10.1021/ja990324r

    Article  CAS  Google Scholar 

  68. Martin, R. and Buchwald, S.L., Acc. Chem. Res., 2008, vol. 41, p. 1461. https://doi.org/10.1021/ar800036s

    Article  CAS  Google Scholar 

  69. Surry, D.S. and Buchwald, S.L., Angew. Chem., Int. Ed., 2008, vol. 47, p. 6338. https://doi.org/10.1002/anie.200800497

    Article  CAS  Google Scholar 

  70. Zhang, J., Chen, J., Liu, M., Zheng, X., Ding, J., and Wu, H., Green Chem., 2012, vol. 14, p. 912. https://doi.org/10.1039/C2GC16539B

    Article  CAS  Google Scholar 

  71. Bahekar, S.S., Sarkate, A.P., Wadhai, V.M., Wakte, P.S., and Shinde, D.B., Catal. Commun., 2013, vol. 41, p. 123. https://doi.org/10.1016/j.catcom.2013.07.019

    Article  CAS  Google Scholar 

  72. Bunnett, J.F. and Zahler, R.E., Chem. Rev., 1951, vol. 49, p. 273. https://doi.org/10.1021/cr60153a002

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

We gratefully acknowledge Prof. Tao Xu (Tongji University), Prof. Xiaoyu Yang (ShanghaiTech University), and Prof. Guoyin Yin (Wuhan University) for helpful discussion and proofreading of the manuscript.

Funding

We are grateful for the financial support from National Natural Science Foundation of China (21801113, 21961020) and the start-up Fund of Nanchang University.

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  1. College of Chemistry, Nanchang University, 330031, Nanchang Jiangxi, China

    Y. Peng, Z. Li, J. Hu & T. Wu

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Peng, Y., Li, Z., Hu, J. et al. Palladium-Catalyzed Denitrative Mizoroki–Heck Reactions of Aryl or Alkyl Olefins with Nitrobenzenes. Russ J Org Chem 58, 1868–1877 (2022). https://doi.org/10.1134/S1070428022120168

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