Bipyridine Ligand-Promoted cis-Selective Hydroboration of Alkynes with Chromium Catalysis

doi:10.6023/cjoc202210006

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (7): 2447-2453.DOI: 10.6023/cjoc202210006 Previous Articles Next Articles

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联吡啶配体促进铬催化炔烃的顺式硼氢化反应

王莎, 陈常鹏, 曾小明^*()

四川大学化学学院成都 610064

收稿日期:2023-05-20 修回日期:2023-06-06 发布日期:2023-06-13
通讯作者: 曾小明
基金资助:
国家自然科学基金(21971168); 国家自然科学基金(22125107)

Bipyridine Ligand-Promoted cis-Selective Hydroboration of Alkynes with Chromium Catalysis

Sha Wang, Changpeng Chen, Xiaoming Zeng()

College of Chemistry, Sichuan University, Chengdu 610064

Received:2023-05-20 Revised:2023-06-06 Published:2023-06-13
Contact: Xiaoming Zeng
Supported by:
National Natural Science Foundation of China(21971168); National Natural Science Foundation of China(22125107)

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Sha Wang, Changpeng Chen, Xiaoming Zeng. Bipyridine Ligand-Promoted cis-Selective Hydroboration of Alkynes with Chromium Catalysis[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2447-2453.

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Fig. & Tab. 5

Scheme 1. Non-precious metal-catalyzed hydroboration of alkynes

Entry Deviation from standard conditions Yield/%

Table 1. Optimization of reaction parameters in the catalytic cis- selective hydroboration of alkynea

Table 2. Cr-catalyzed cis-selective hydroboration of alkynes for the synthesis of olefinated boronate esters

Scheme 2. Preliminary mechanistic studies

Scheme 3. Gram-scale hydroboration and synthetic applications

References 16

[1]	Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. doi: 10.1021/cr00039a007
[2]	(a) Roscales, S.; Csaký, A. G. Chem. Soc. Rev. 2014, 43, 8215. doi: 10.1039/c4cs00195h pmid: 25181967
	(b) Leonori, D.; Aggarwal, V. K. Angew. Chem. Int. Ed. 2015, 54, 1082. doi: 10.1002/anie.201407701 pmid: 25181967
[3]	(a) Revunova, K.; Nikonov, G. I. Dalton Trans. 2015, 44, 840. doi: 10.1039/c4dt02024c pmid: 25384615
	(b) Rochat, R.; Lopez, M. J.; Tsurugi, H.; Mashima, K. ChemCatChem 2016, 8, 10. doi: 10.1002/cctc.v8.1 pmid: 25384615
[4]	(a) Arrowsmith, M.; Hadlington, T. J.; Hill, M. S.; KociokKohn, G. Chem. Commun. 2012, 48, 4567. doi: 10.1039/c2cc30565h pmid: 23307492
	(b) Arrowsmith, M.; Hill, M. S.; Kociok-Kchn, G. Chem.-Eur. J. 2013, 19, 2776. doi: 10.1002/chem.201203190 pmid: 23307492
	(c) Mukherjee, D.; Ellern, A.; Sadow, A. D. Chem. Sci. 2014, 5, 959. doi: 10.1039/C3SC52793J pmid: 23307492
	(d) Fohlmeister, L.; Stasch, A. Chem. Eur. J. 2016, 22, 10235. doi: 10.1002/chem.v22.29 pmid: 23307492
[5]	(a) Kim, H. R.; Yun, J. Chem. Commun. 2011, 47, 2943. doi: 10.1039/C0CC04496B pmid: 30942593
	(b) Yuan, W.; Ma, S. Org. Biomol. Chem. 2012, 10, 7266. doi: 10.1039/c2ob26147b pmid: 30942593
	(c) Hall, J. W.; Unson, D. M. L.; Brunel, P.; Collins, L. R.; Cybulski, M. K.; Mahon, M. F.; Whittlesey, M. K. Organometallics 2018, 37, 3102. doi: 10.1021/acs.organomet.8b00467 pmid: 30942593
	(d) Bao, H.; Zhou, B.; Jin, H.; Liu, Y. J. Org. Chem. 2019, 84, 3579. doi: 10.1021/acs.joc.9b00321 pmid: 30942593
	(e) Armstrong, M. K.; Lalic, G. J. Am. Chem. Soc. 2019, 141, 6173. doi: 10.1021/jacs.9b02372 pmid: 30942593
[6]	(a) Greenhalgh, M. D.; Thomas, S. P. Chem. Commun. 2013, 49, 11230. doi: 10.1039/c3cc46727a pmid: 30376317
	(b) Nakajima, K.; Kato, T.; Nishibayashi, Y. Org. Lett. 2017, 19, 4323. doi: 10.1021/acs.orglett.7b01995 pmid: 30376317
	(c) Myhill, J. A.; Wilhelmsen, C. A.; Zhang, L.; Morken., J. P. J. Am. Chem. Soc. 2018, 140, 15181. doi: 10.1021/jacs.8b09909 pmid: 30376317
[7]	(a) Chen, J.; Shen, X.; Lu, Z. Angew. Chem., Int. Ed. 2021, 60, 690. doi: 10.1002/anie.v60.2 pmid: 29906339
	(b) Bismuto, A.; Thomas, S. P.; Cowley, M. J. Angew. Chem., Int. Ed. 2016, 55, 15356. doi: 10.1002/anie.v55.49 pmid: 29906339
	(c) Ben-Daat, H.; Rock, C. L.; Flores, M.; Groy, T. L.; Bowman, A. C.; Trovitch, R. J. Chem. Commun. 2017, 53, 7333. doi: 10.1039/C7CC02281F pmid: 29906339
	(d) Guo, J.; Cheng, B.; Shen, X.; Lu, Z. J. Am. Chem. Soc. 2017, 139, 15316. doi: 10.1021/jacs.7b09832 pmid: 29906339
	(e) Victoria, A.; Pollard, M.; Angeles, F.; Alan, R.; Kennedy, R. M.; Mulvey, R. E. Angew. Chem. Int. Ed. 2018, 57, 10651. doi: 10.1002/anie.201806168 pmid: 29906339
	(f) Magre, M.; Maity, B.; Falconnet, A.; Cavallo, L.; Rueping, M. Angew. Chem. Int. Ed. 2019, 58, 1. pmid: 29906339
[8]	Mandal, S.; Kumar Verma, P.; Geetharani, K. Chem. Commun. 2018, 54, 13690. doi: 10.1039/C8CC08361D
[9]	Minami, H.; Saito, T.; Wang, C.; Uchiyama, M. Angew. Chem., Int. Ed. 2015, 54, 4665. doi: 10.1002/anie.201412249
[10]	Fleige, M.; Mobus, J.; Stein, T.; Glorius, F.; Stephan, D. W. Chem. Commun. 2016, 52, 10830. doi: 10.1039/C6CC05360B
[11]	Iwadate, N.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 2548. doi: 10.1021/ja1000642
[12]	(a) Agapie, T. Coord. Chem. Rev. 2011, 255, 861. doi: 10.1016/j.ccr.2010.11.035
	(b) Li, J.; Knochel, P. Synthesis 2019, 51, 2100. doi: 10.1055/s-0037-1611756
	(c) Zeng, X. Synlett 2020, 31, 205. doi: 10.1055/s-0039-1690764
	(d) Cong, X.; Zeng, X. Acc. Chem. Res. 2021, 54, 2014. doi: 10.1021/acs.accounts.1c00096
[13]	(a) Cong, X.; Tang, H.; Zeng, X. J. Am. Chem. Soc. 2015, 137, 14367. doi: 10.1021/jacs.5b08621 pmid: 31074625
	(b) Steib, A. K.; Kuzmina, O. M.; Fernandez, S.; Malhotra, S.; Knochel, P. Chem. Eur. J. 2015, 21, 1961. doi: 10.1002/chem.v21.5 pmid: 31074625
	(c) Yan, J.; Yoshikai, N. Org. Lett. 2017, 19, 6630. doi: 10.1021/acs.orglett.7b03342 pmid: 31074625
	(d) Han, B.; Ma, P.; Cong, X.; Chen, H.; Zeng, X. J. Am. Chem. Soc. 2019, 141, 9018. doi: 10.1021/jacs.9b03328 pmid: 31074625
	(e) Yin, J.; Li, J.; Wang, G.-X.; Yin, Z.-B.; Zhang, W.-X.; Xi, Z. J. Am. Chem. Soc. 2019, 141, 4241. doi: 10.1021/jacs.9b00822 pmid: 31074625
	(f) Tang, J.; Liu, L. L.; Yang, S.; Cong, X.; Luo, M.; Zeng, X. J. Am. Chem. Soc. 2020, 142, 7715. doi: 10.1021/jacs.0c00283 pmid: 31074625
	(g) Chen, M.; Doba, T.; Sato, T.; Razumkov, H.; Ilies, L.; Shang, R.; Nakamura, E. J. Am. Chem. Soc. 2020, 142, 4883. doi: 10.1021/jacs.0c00127 pmid: 31074625
	(h) Zhao, L.; Hu, C.; Cong, X.; Deng, G.; Liu, L. L.; Luo, M.; Zeng, X. J. Am. Chem. Soc. 2021, 143, 1618. doi: 10.1021/jacs.0c12318 pmid: 31074625
	(i) Zhang, Y.; Zhu, S. Chin. J. Org. Chem. 2021, 41, 1255. doi: 10.6023/cjoc202100017 pmid: 31074625
	(j) Ye, Y.; Gong, H. Chin. J. Org. Chem. 2020, 40, 2588. doi: 10.6023/cjoc202000048 pmid: 31074625
	(k) Zhao, Y.; Ge, S. Angew. Chem. Int. Ed. 2021, 60, 2149. doi: 10.1002/anie.v60.4 pmid: 31074625
[14]	Shima, T.; Yang, J.; Luo, G.; Luo, Y.; Hou, Z. J. Am. Chem. Soc. 2020, 142, 9007.. doi: 10.1021/jacs.0c02939
[15]	Gong, L.; Li, C.; Yuan, F.; Liu, S.; Zeng, X. Org. Lett. 2022, 24, 3227. doi: 10.1021/acs.orglett.2c01015
[16]	(a) Zhang, Y.-D.; Li, X.-Y.; Mo, Q.-K.; Shi, W.-B.; Zhao, J.-B.; Zhu, S.-F. Angew. Chem. Int. Ed. 2022, 61, e202208473. doi: 10.1002/anie.202200599 pmid: 35104020
	(b) Zhou, F.; Shi, W.; Liao, X.; Yang, Y.; Yu, Z.; You, J. ACS Catal. 2022, 12, 676. doi: 10.1021/acscatal.1c04549 pmid: 35104020
	(c) Brzozowska, A.; Zubar, V.; Ganardi, R.-C; Rueping, M. Org. Lett. 2020, 22, 3765. doi: 10.1021/acs.orglett.0c00941 pmid: 35104020
	(d) 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. doi: 10.1039/C4CC00550C pmid: 35104020
	(e) Salvado, O.; Fernández, E. Chem. Commun., 2021, 57, 6300. doi: 10.1039/D1CC01882E pmid: 35104020
	(f) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Org. Chem. 1987, 52, 1276. doi: 10.1021/jo00383a019 pmid: 35104020
	(g) Garhwal, S.; Fridman, N.; de Ruiter, G. Inorg. Chem. 2020, 59, 13817. doi: 10.1021/acs.inorgchem.0c02057 pmid: 35104020

联吡啶配体促进铬催化炔烃的顺式硼氢化反应

Bipyridine Ligand-Promoted cis-Selective Hydroboration of Alkynes with Chromium Catalysis

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References 16

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