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Research Progress of Transition Metal-Catalyzed Synthesis of 1,3-Conjugated Dienyl Boron Compounds

  • Guangli Xu ,
  • Hongping Han ,
  • Luwei Cao ,
  • Simin Hong ,
  • linyue Hai ,
  • Xiang Cui
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  • a College of Chemistry & Chemical Engineering, Qinghai Normal University, Xining 810000
    b Academy of Plateau Science and Sustainability, Xining 81000
    c Qinghai Key Laboratory of Advanced Technology and Application of Environmental Functional Materials, Xining 810016

Received date: 2023-10-07

  Revised date: 2023-12-12

  Online published: 2023-12-21

Supported by

Natural Science Foundation of Qinghai Province(2024-ZJ-998); Young and Middle-Aged Science Foundation of Qinghai Normal University(2023QZR017)

Abstract

1,3-Dienyl boron compounds have important applications in the modification of biologically active molecules and organic synthesis. It can be used as an organoboron reagent to construct a new organic framework by Suzuki reaction, and and can also undergo Diels-Alder reaction to prepare boron substituted cycloolefin intermediates. At present, the synthesis of 1,3-conjugated dienyl boron compounds is mainly achieved through the cross-coupling reaction of organometallic reagents to alkynes or olefin catalyzed by transition metals, the Heck reaction of borates to olefin, the hydroboration of alkynes and the carboboration of alkynes. The synthesis of 1,3-conjugated dienyl boron compounds is reviewed by classification based on different reaction types catalyzed by transition metals, and its development prospects are prospected.

Cite this article

Guangli Xu , Hongping Han , Luwei Cao , Simin Hong , linyue Hai , Xiang Cui . Research Progress of Transition Metal-Catalyzed Synthesis of 1,3-Conjugated Dienyl Boron Compounds[J]. Chinese Journal of Organic Chemistry, 2024 , 44(5) : 1480 -1493 . DOI: 10.6023/cjoc202310008

References

[1]
(a) Grigalunas, M.; Ankner, T.; Norrby, P.-O.; Wiest, O.; Helquist, P. Org. Lett. 2014, 16, 3970.
[1]
(b) Huang, E.; Bunel, E.; Faul, M. F. Org. Lett. 2007, 9, 4343.
[2]
(a) Nicholas, C. P. Appl. Catal., A 2017, 543, 82.
[2]
(b) Kotha, S.; Meshram, M. Chem.-Asian J. 2018, 13, 1758.
[3]
(a) Sun, H.; Liang, Y.; Thompson, M. P.; Gianneschi, N. C. Prog. Polym. Sci. 2021, 120, 101427.
[3]
(b) Chen, M.; Yang, B.; Chen, C. Synlett 2016, 27, 1297.
[3]
(c) Ishii, S.; Ota, Y.; Matsuoka, S.; Suzuki, M. ACS Appl. Polym. Mater. 2023, 5, 7614.
[4]
Chen, J.-M.; Yu, B.; Wei, Y.-M. Appl. Energy 2018, 224, 160.
[5]
(a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
[5]
(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[5]
(c) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
[5]
(d) Wang, J.; Sánchez-Roselló, M.; Ace?a, J. L.; Pozo, C.; rochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
[5]
(e) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Ace?a, J. L.; loshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422.
[5]
(f) Hu, J.; Yang, Y.; Lou, Z.; Ni, C.; Hu, J. Chin. J. Chem. 2018, 36, 1202.
[6]
(a) Hedhli, A.; Baklouti, A. Tetrahedron Lett. 1995, 36, 4433.
[6]
(b) Sporn, M. B.; Dunlop, N. M.; Newton, D. L.; Henderson, W. R. Nature 1976, 263, 110.
[6]
(c) Zhu, Y.; Liu, R. S. H. Biochemistry 1993, 32, 10233.
[6]
(d) Chopra, D. P.; Wilkoff, W. J. Eur. J. Cancer 1979, 15, 1417.
[6]
(e) Srisethnil, S. J. Med. Chem. 1979, 22, 1059.
[7]
(a) Ohmura, T.; Masuda, K.; Takase, I.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 16624.
[7]
(b) Abbas, S. Y.; Zhao, P.; Overman, L. E. Org. Lett. 2018, 20, 868.
[8]
(a) Pyziak, J.; Walkowiak, J.; Marciniec, B. Chem.-Eur. J. 2017, 23, 3502.
[8]
(b) Sardini, S. R.; Lambright, A. L.; Trammel, G. L.; Omer, H. M.; Liu, P.; Brown, M. K. J. Am. Chem. Soc. 2019, 141, 9391.
[8]
(c) Yang, C.; Gao, Y.; Bai, S.; Jiang, C.; Qi, X. J. Am. Chem. Soc. 2020, 142, 11506.
[9]
(a) Stikute, A.; Turks, M. Tetrahedron Lett. 2017, 58, 2727.
[9]
(b) Mario Altendorfera M; Menche, D. Chem. Commun. 2012, 48, 8267.
[9]
(c) Gan, Y.; Hu, H.; Liu, Y.-H. Org. Lett. 2020, 22, 4418.
[10]
(a) Reid, W. B.; Spillane, J. J.; Krause, S. B.; Watson, D. A. J. Am. Chem. Soc. 2016, 138, 17, 5539.
[10]
(b) Lovinger, G. J.; Aparece, M. D.; Morken, J. P. J. Am. Chem. Soc. 2017, 139, 3153.
[11]
Altendorfera, M.; Menche, D. Chem. Commun. 2012, 48, 8267.
[12]
(a) Jiang, B.; Liang, Q. J.; Han, Y. Org. Lett. 2018, 20, 3215.
[12]
(b) Kischkewitz, M.; Gerleve, C.; Studer, A. Org. Lett. 2018, 20, 3666.
[12]
(c) Tripathi, C. B.; Mukherjee, S. Org. Lett. 2015, 17, 4424.
[12]
(d) Dada, R.; Wei, Z.; Gui, R. Angew. Chem., Int. Ed. 2018, 57, 3981.
[13]
(a) Yang, X. H.; Dong, V. M. J. Am. Chem. Soc. 2017, 139, 1774.
[13]
(b) Marcum, J. S.; Roberts, C. C.; Manan, R. S. J. Am. Chem. Soc. 2017, 139, 15580.
[13]
(c) Roberts, C. C.; Matías, D. M.; Goldfogel, M. J. J. Am. Chem. Soc. 2015, 137, 6488.
[14]
(a) Guillam, A.; Toupet, L.; Maddaluno, J. J. Org. Chem. 1998, 63, 5110.
[14]
(b) Gulías, M.; Durán, J.; López, F. J. Am. Chem. Soc. 2007, 129, 11026.
[14]
(c) Fujiwara, K.; Kurahashi, T.; Matsubara, S. Org. Lett. 2010, 12, 4548.
[14]
(d) Liu, L.; Kim, H.; Xie, Y. J. Am. Chem. Soc. 2017, 139, 13656.
[15]
(a) Barluenga, J.; Tomás, G. M.; Aznar, F. Adv. Synth. Catal. 2010, 352, 3235.
[15]
(b) Zhang, X. M.; Yang, J.; Zhuang, Q. B. ACS Catal. 2018, 8, 6094.
[15]
(c) Kreyenschmidt, F.; Koszinowsk, K. Chem.-Eur. J. 2018, 24, 1168.
[16]
(a) Lopez, S. J. A.; Lamberti, M.; Pappalardo, D. Macromol 2003, 36, 9260.
[16]
(b) Milione, S.; Cuomo, C.; Capacchione, C. Macromol 2007, 40, 5638.
[16]
(c) Luo, K.; Kim, S. J.; Cartwright, A. N. Macromol 2011, 44, 4665.
[16]
(d) Bonnet, F.; Jones, C. E.; Semlali, C. Dalton Trans. 2013, 42, 790.
[16]
(e) Kostjuk, S. V. RSC Adv. 2015, 5, 13125.
[17]
Eberlin, L.; Tripoteau, F.; Carreaux, F.; Whiting, A.; Carboni, B. J. Org. Chem. 2014, 10, 237.
[18]
Wang, C.; Tobrman, T.; Xu, Z.; Negishi, E. Org. Lett. 2009, 18, 4092.
[19]
Vargo, T. R.; Hale, J. S.; Nelson, S. G. Angew. Chem., Int. Ed. 2010, 49, 8678.
[20]
(a) Wang, Y.; Wu, Y.; Li, Y.; Tang, Y. Chem. Sci. 2017, 8, 3852.
[20]
(b) Sakakibara, R.; Itoh, K.; Fujii, H. J. Org. Chem. 2019, 84, 18, 11474.
[21]
(a) Manolikakes, G.; Knochel, P. Angew. Chem., Int. Ed., 2008, 48, 205.
[21]
(b) Arthurs, R. A.; Hughes, D. L.; Richards, C. J. Eur. J. Inorg. Chem. 2022, 2022, e202101077.
[22]
(a) Liu, Z.; Luan, N.; Shen, L.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. J. Org. Chem. 2019, 84, 12358.
[22]
(b) Goebel, J. F.; Zeng, Z.; Handelmann, J.; Hermann, A.; Rodstein, I.; Gensch, T.; Gessner, V. H.; L?ffler, L. Angew. Chem., Int. Ed. 2023, 62, e202216160
[23]
(a) Chishiro, A.; Konishi, M.; Inaba, R.; Yumura, T.; Imoto, H.; Naka, K. Dalton Trans. 2022, 51, 95.
[23]
(b) Chang, Y.-T.; Liu, L.-J.; Peng, W.-S.; Lin, L.-T.; Chan, Y.-T.; Tsai, F.-Y. J. Chin. Chem. Soc. 2021, 68, 469.
[24]
(a) Wang, X.; Sun, H.; Liu, J.; Zhong, W.; Zhang, M.; Zhou, H.; Dai, D.; Lu, X. Org. Lett. 2019, 21, 719.
[24]
(b) Markham, T. E.; Duggan, P. J.; Johnston, M. R. Tetrahedron 2023, 130, 133160
[25]
Stewart, S. K.; Whiting, A. Tetrahedron Lett. 1995, 36, 3925.
[26]
Coleman, R. S.; Walczak, M. C. Org. Lett. 2005, 7, 2289.
[27]
(a) Maikhuri, V. K.; Maity, J.; Srivastavac, S.; Prasad, A. K. Org. Biomol. Chem. 2022, 20, 9522.
[27]
(b) Dang, H. T.; Nguyen, V. D.; Pham, H. H.; Arman, H. D.; Larionov, O. V. Tetrahedron 2019, 75, 3258
[28]
Daini, M.; Suginome, M. Chem. Commun. 2008, 5224.
[29]
Wang, C.; Tobrman, T.; Xu, Z.; Negishi, E. Org. Lett. 2009, 11, 4092.
[30]
Negishi, E.; Tobrman, T.; Rao, H.; Xu, S.; Lee, C.-T. Isr. J. Chem. 2010, 50, 696.
[31]
Wang, C.; Xu, Z.; Tobrman, T.; Negishi, E. Adv. Synth. Catal. 2010, 352, 627.
[32]
Singidi, R. R.; RajanBabu, T. V. Org. Lett. 2010, 12, 2622.
[33]
Xu, S.; Zhang, Y.; Li, B.; Liu, S.-Y. J. Am. Chem. Soc. 2016, 138, 14566.
[34]
Wang, Z.; Wu, J.; Lamine, W.; Li, B., Sotiropoulos, J.-M.; Chrostowska, A.; Miqueu, K.; Liu, S.-Y. Angew. Chem., Int. Ed. 2021, 60, 21231.
[35]
Wang, Z.; Lamine, W. M.; Liu, S.-Y. Chem. Sci. 2023, 14, 2082.
[36]
Sasaki, Y.; Horita, Y.; Zhong, C.; Sawamura, M.; Ito, H. Angew. Chem., Int. Ed. 2011, 50, 2778.
[37]
Xu, H.-D.; Wu, H.; Jiang, C.; Chen, P.; Shen, M.-H. Tetrahedron Lett. 2016, 57, 2915.
[38]
Tai, C.-C.; Yu, M.-S.; Chen, Y.-L.; Chuang, W.-H.; Lin, T.-H. Yap, G. P. A.; Ong, T.-G. Chem. Commun. 2014, 50, 4344.
[39]
Mohan, B.; Park, K. H. Appl. Catal.,A 2016, 519, 78.
[40]
Moncomble, A.; Floch, P. L.; Lledos, A.; Gosmini, C. J. Org. Chem. 2012, 77, 5056.
[41]
Bassler, D. P.; Alwali, A.; Spence, L.; Beale, O.; Beng, T. K. J. Organomet. Chem. 2015, 780, 6.
[42]
Huang, Q.; Hu, M.-Y.; Zhu, S.-F. Org. Lett. 2019, 21, 7883.
[43]
Alfaro, R.; Parra, A.; Aleman, J.; Ruano, J. L. G.; Tortosa, M. J. Am. Chem. Soc. 2012, 134, 15165.
[44]
Rivera-Chao, E.; Mastral, M. Angew. Chem., Int. Ed. 2018, 57, 9945.
[45]
Gali?anes, V.-N.; Mastral, M. F. ChemCatChem 2018, 10, 4817.
[46]
Xu, W.-Y.; Li, Y.-J.; Gong, T.-J.; Fu, Y. Org. Lett. 2022, 24, 5884.
[47]
Walkowiak, J.; Jankowska-Wajda, M.; Marciniec, B. Chem.- Eur. J. 2008, 14, 6679.
[48]
Pyziak, J.; Walkowiak, J.; Hoffmann, M.; Marciniec, B. J. Organomet. Chem. 2015, 794, 96e103
[49]
Hirano, M.; Kuramochi, A.; Shimada, K.; Komine, N.; Kiyota, S.; Westcott, S. A. Chem. Commun. 2019, 55, 10527.
[50]
Rohde, L. N.; Diver, S. T. J. Org. Chem. 2022, 87, 14078.
[51]
Kirai, N.; Iguchi, S.; Ito, T.; Takaya, J.; Iwasawa, N. Bull. Chem. Soc. Jpn. 2013, 86, 784.
[52]
Funk, T. W.; Efskind, J.; Grubbs, R. H. Org. Lett. 2005, 7, 187.
[53]
Zhang, L.; Yan, J.; Ahmadli, D.; Wang, Z.; Ritter, T. J. Am. Chem. Soc. 2023, 145, 20182.
[54]
Jia, J.; Yuan, F.; Zhang, Z.; Song, X.; Hu, F.; Xia, Y. Org. Lett. 2022, 24, 1985.
[55]
Gerdin, M.; Moberg, C. Org. Lett. 2006, 8, 2929.
[56]
Pang, X.; Shu, X.-Z. Chin. J. Chem. 2023, 41, 1637
[57]
Xu, G.-L.; Liu, C.-Y.; Pang, X.; Liu, X.-Y.; Shu, X.-Z. CCS Chem. 2022, 4, 864.
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