过渡金属催化1,3-共轭二烯基硼化合物合成研究进展

doi:10.6023/cjoc202310008

摘要/Abstract

1,3-二烯基硼化合物在生物活性分子修饰和有机合成中具有重要应用, 可以作为有机硼试剂通过Suzuki反应构建新的有机框架, 也可以发生Diels-Alder环加成反应来制备硼代环烯烃中间体. 目前共轭烯基硼化合物的合成一般是通过过渡金属催化有机金属试剂对炔烃或烯烃的交叉偶联反应、硼酸酯对烯烃的Heck反应、烯炔硼氢化反应或烯炔碳硼化反应实现. 以过渡金属催化的不同反应类型为主线, 分类对1,3-共轭二烯基硼化合物的合成进行了综述, 并对其发展前景予以展望.

关键词: 过渡金属, 催化, 1,3-共轭二烯基硼, 硼氢化, 碳硼化

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.

Key words: transition metal, catalysis, 1,3-conjugated dienyl boron, hydroboration, carboboration

引用此文

徐光利, 韩鸿萍, 曹露微, 洪思敏, 海林悦, 崔香. 过渡金属催化1,3-共轭二烯基硼化合物合成研究进展[J]. 有机化学, 2024, 44(5): 1480-1493.

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.

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图/表 22

图1. 共轭烯烃天然产物

Figure 1. Conjugated alkenes natural products

图式1. 钯催化烯基硼与烯基碘Heck反应合成1,3-共轭二烯基硼化合物

Scheme 1. Palladium-catalyzed Heck reaction of alkenyl boron with alkenyl iodine to synthesize 1,3-conjugated dienyl boron compounds

图式2. 钯催化Stille偶联反应合成1,3-共轭二烯基硼化合物

Scheme 2. Palladium-catalyzed Stille coupling reaction to synthesize 1,3-conjugated dienyl boron compounds

图式3. 钯催化有机锆试剂参与的炔烃双官能团化反应合成1,3-共轭二烯基硼化合物

Scheme 3. Palladium-catalyzed difunctional reaction of alkyne involving organozirconium reagent to synthesize 1,3-conjugated dienyl boron compounds

图式4. 钯催化有机锌试剂参与的Negishi偶联反应合成1,3-共轭二烯基硼化合物

Scheme 4. Palladium-catalyzed Negishi coupling reaction involving organozinc reagents to synthesize 1,3-conjugated dienyl boron compounds

图式5. 钯催化有机硼硅试剂参与烯炔双官能团化反应合成1,3-共轭二烯基硼化合物

Scheme 5. Palladium-catalyzed difunctional reaction of alkyne involving borosilicon reagent to synthesize 1,3-conjugated dienyl boron compounds

图式6. 钯催化烯炔硼氢化反应合成1,3-共轭二烯基硼化合物

Scheme 6. Palladium-catalyzed hydroboration of alkyne to synthesize 1,3-conjugated dienyl boron compounds

图式7. 铜催化烯炔硼氢化反应合成1,3-共轭二烯基硼化合物

Scheme 7. Copper-catalyzed hydroboration of enyl to synthesize 1,3-conjugated dienyl boron compounds

图式8. 铜催化取代烯炔硼氢化反应合成1,3-共轭二烯基硼化合物

Scheme 8. Copper-catalyzed hydroboration of substituted alkyne to synthesize 1,3-conjugated dienyl boron compounds

图式9. 铜催化炔烃硼氢化反应合成1,3-共轭二烯基硼化合物

Scheme 9. Copper-catalyzed hydroboration of alkyne to synthesize 1,3-conjugated dienyl boron compounds

图式10. 钴催化1,6-二炔硼氢化环化反应合成1,3-二烯基硼化合物

Scheme 10. Cobalt-catalyzed hydrogenation cyclization of 1,6-diynylboron to synthesize 1,3-conjugated dienyl boron com- pounds

图式11. 铜催化烯炔碳硼化反应合成1,3-共轭二烯基硼化合物

Scheme 11. Copper-catalyzed carboboration of olefin acetylene to synthesize 1,3-conjugated dienyl boron compounds

图式12. 铜催化炔烃碳硼化反应合成1,3-共轭二烯基硼化合物

Scheme 12. Copper-catalyzed carboboration of alkyne to synthesize 1,3-conjugated dienyl boron compounds

图式13. 铜、钯共催化炔烃与烯基溴和双(频哪醇)二硼的烯基硼化反应合成1,3-二烯基硼化合物

Scheme 13. Cu/Pd-catalyzed alkenylboration of alkynes with alkenyl bromides and bis(pinacolato)diboron to synthesize 1,3-conjugated dienyl boron compounds

图式14. 铜、钯共催化炔烃双官能团化反应合成1,3-共轭二烯基硼化合物

Scheme 14. Cu/Pd-catalyzed bifunctional reaction of alkynes to synthesize 1,3-conjugated dienyl boron compounds

图式15. 钌催化烯烃与炔烃交叉还原偶联反应合成1,3-共轭二烯基硼化合物

Scheme 15. Ruthenium-catalyzed cross-reduction coupling reaction of alkenes and alkynes to synthesize 1,3-conjugated dienyl boron compounds

图式16. 钌催化烯烃与炔烃交叉还原偶联反应合成1,3-共轭二烯基硼化合物

Scheme 16. Ruthenium-catalyzed cross-reduction coupling reaction of alkenes and alkynes to synthesize 1,3-conjugated dienyl boron compounds

图式17. 钯催化共轭二烯脱氢硼化反应合成1,3-共轭二烯基硼化合物

Scheme 17. Palladium-catalyzed dehydroborylation of conjugated dienes to synthesize 1,3-conjugated dienyl boron compounds

图式18. 钌催化烯烃复分解反应合成1,3-共轭二烯基硼化合物

Scheme 18. Ruthenium-catalyzed metathesis reaction of olefin to synthesize 1,3-conjugated dienyl boron compounds

图式19. 铜催化二氟环丁烯开环去氟硼化反应合成1,3-二烯基硼化合物

Scheme 19. Copper-catalyzed ring-opening defluoroboronation reaction of difluorocyclobutene to synthesize 1,3-conjugated dienyl boron compounds

图式20. 镍催化烯烃硼氢化反应合成1,3-共轭二烯基硼化合物

Scheme 20. Nickel-catalyzed hydroboration of olefin to synthesize 1,3-conjugated dienyl boron compounds

图式21. 镍催化烯基亲电试剂还原偶联反应合成1,3-二烯基硼化合物

Scheme 21. Nickel-catalyzed reduction coupling of alkenyl electrophiles to synthesize 1,3-conjugated dienyl boron compounds

参考文献 57

[1]	(a) Grigalunas, M.; Ankner, T.; Norrby, P.-O.; Wiest, O.; Helquist, P. Org. Lett. 2014, 16, 3970. doi: 10.1021/ol5017965 pmid: 25032503
	(b) Huang, E.; Bunel, E.; Faul, M. F. Org. Lett. 2007, 9, 4343. pmid: 25032503
[2]	(a) Nicholas, C. P. Appl. Catal., A 2017, 543, 82.
	(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.
	(b) Chen, M.; Yang, B.; Chen, C. Synlett 2016, 27, 1297.
	(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. doi: 10.1126/science.1131943 pmid: 26756377
	(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. pmid: 26756377
	(c) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315. doi: 10.1021/acs.jmedchem.5b00258 pmid: 26756377
	(d) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; Pozo, C.; rochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432. pmid: 26756377
	(e) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Aceña, J. L.; loshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422. doi: 10.1021/acs.chemrev.5b00392 pmid: 26756377
	(f) Hu, J.; Yang, Y.; Lou, Z.; Ni, C.; Hu, J. Chin. J. Chem. 2018, 36, 1202. pmid: 26756377
[6]	(a) Hedhli, A.; Baklouti, A. Tetrahedron Lett. 1995, 36, 4433. pmid: 8399151
	(b) Sporn, M. B.; Dunlop, N. M.; Newton, D. L.; Henderson, W. R. Nature 1976, 263, 110. pmid: 8399151
	(c) Zhu, Y.; Liu, R. S. H. Biochemistry 1993, 32, 10233. pmid: 8399151
	(d) Chopra, D. P.; Wilkoff, W. J. Eur. J. Cancer 1979, 15, 1417. pmid: 8399151
	(e) Srisethnil, S. J. Med. Chem. 1979, 22, 1059. pmid: 8399151
[7]	(a) Ohmura, T.; Masuda, K.; Takase, I.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 16624.
	(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.
	(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.
	(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. pmid: 32427489
	(b) Mario Altendorfera M; Menche, D. Chem. Commun. 2012, 48, 8267. pmid: 32427489
	(c) Gan, Y.; Hu, H.; Liu, Y.-H. Org. Lett. 2020, 22, 4418. doi: 10.1021/acs.orglett.0c01424 pmid: 32427489
[10]	(a) Reid, W. B.; Spillane, J. J.; Krause, S. B.; Watson, D. A. J. Am. Chem. Soc. 2016, 138, 17, 5539. pmid: 28161943
	(b) Lovinger, G. J.; Aparece, M. D.; Morken, J. P. J. Am. Chem. Soc. 2017, 139, 3153. doi: 10.1021/jacs.6b12663 pmid: 28161943
[11]	Altendorfera, M.; Menche, D. Chem. Commun. 2012, 48, 8267.
[12]	(a) Jiang, B.; Liang, Q. J.; Han, Y. Org. Lett. 2018, 20, 3215. doi: 10.1021/acs.orglett.8b01067 pmid: 26382149
	(b) Kischkewitz, M.; Gerleve, C.; Studer, A. Org. Lett. 2018, 20, 3666. doi: 10.1021/acs.orglett.8b01459 pmid: 26382149
	(c) Tripathi, C. B.; Mukherjee, S. Org. Lett. 2015, 17, 4424. doi: 10.1021/acs.orglett.5b02026 pmid: 26382149
	(d) Dada, R.; Wei, Z.; Gui, R. Angew. Chem., Int. Ed. 2018, 57, 3981. pmid: 26382149
[13]	(a) Yang, X. H.; Dong, V. M. J. Am. Chem. Soc. 2017, 139, 1774.
	(b) Marcum, J. S.; Roberts, C. C.; Manan, R. S. J. Am. Chem. Soc. 2017, 139, 15580.
	(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. pmid: 20863073
	(b) Gulías, M.; Durán, J.; López, F. J. Am. Chem. Soc. 2007, 129, 11026. pmid: 20863073
	(c) Fujiwara, K.; Kurahashi, T.; Matsubara, S. Org. Lett. 2010, 12, 4548. doi: 10.1021/ol101842y pmid: 20863073
	(d) Liu, L.; Kim, H.; Xie, Y. J. Am. Chem. Soc. 2017, 139, 13656. pmid: 20863073
[15]	(a) Barluenga, J.; Tomás, G. M.; Aznar, F. Adv. Synth. Catal. 2010, 352, 3235. pmid: 29110364
	(b) Zhang, X. M.; Yang, J.; Zhuang, Q. B. ACS Catal. 2018, 8, 6094. pmid: 29110364
	(c) Kreyenschmidt, F.; Koszinowsk, K. Chem.-Eur. J. 2018, 24, 1168. doi: 10.1002/chem.201704547 pmid: 29110364
[16]	(a) Lopez, S. J. A.; Lamberti, M.; Pappalardo, D. Macromol 2003, 36, 9260. pmid: 23202137
	(b) Milione, S.; Cuomo, C.; Capacchione, C. Macromol 2007, 40, 5638. pmid: 23202137
	(c) Luo, K.; Kim, S. J.; Cartwright, A. N. Macromol 2011, 44, 4665. pmid: 23202137
	(d) Bonnet, F.; Jones, C. E.; Semlali, C. Dalton Trans. 2013, 42, 790. doi: 10.1039/c2dt31624b pmid: 23202137
	(e) Kostjuk, S. V. RSC Adv. 2015, 5, 13125. pmid: 23202137
[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.
	(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.
	(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.
	(b) Goebel, J. F.; Zeng, Z.; Handelmann, J.; Hermann, A.; Rodstein, I.; Gensch, T.; Gessner, V. H.; Löffler, 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.
	(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.
	(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. pmid: 15901191
[27]	(a) Maikhuri, V. K.; Maity, J.; Srivastavac, S.; Prasad, A. K. Org. Biomol. Chem. 2022, 20, 9522. doi: 10.1039/d2ob01646j pmid: 36412483
	(b) Dang, H. T.; Nguyen, V. D.; Pham, H. H.; Arman, H. D.; Larionov, O. V. Tetrahedron 2019, 75, 3258 pmid: 36412483
[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. doi: 10.1021/jo3005149 pmid: 22591028
[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. doi: 10.1002/anie.201806334 pmid: 29905396
[45]	Galiñanes, 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. doi: 10.1021/jacs.3c07119 pmid: 37695320
[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.