Chinese Journal of Organic Chemistry >
E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C6F5)3]–
Received date: 2022-05-18
Revised date: 2022-07-20
Online published: 2022-08-25
Supported by
National Natural Science Foundation of China(21542011); Science and Technology Department of Sichuan Province(2020YJ0358); Scientific Research Fund of Leshan Normal University(DGZZ202018); Scientific Research Fund of Leshan Normal University(TRCWYFZCH2019006); Scientific Research Fund of Leshan Normal University(2021SSDJS015); Scientific Research Fund of Leshan Normal University(2021SSDJS016)
The difunctionalization of alkenes and alkynes is a simple and powerful strategy for the synthesis of various organic compounds and has been used to synthesize various important natural products, drug molecules and fine chemical products. The different effects of halo anions, substrates, solvents, temperature and reaction time to the stereospecific and reactivities of 1,1-carboborations of alkynes and B(C6F5)s were studied, meanwhile the corresponding catalytic mechanisum has been expoled. A convenient large-scale preparation method for the stereoselective (E)-1,1-carboboration products has been developed. The catalytic reactivities of ring-opening polymerization of cyclohexene oxide (CHO) have also been explored with different stereo-carboboranes isolated from 1,1-carboboration reaction, and it is noted that the stereospecificity E- or Z- has shown ambiguously different activities. To develop a stereo-specific approach in the synthesis of vinylboranes will not only be very important for the difunctionalization of alkenes and alkynes, but also for the novel stereospecificity organoborons.
Key words： 1,1-carboboration; stereospecificity; alkynes; borane; reactivity
Chong Tian , Qi Sun , Junfeng Wang , Qiao Chen , Zhiguo Wen , Maxim Borzov , Wanli Nie . E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C6F5)3]–[J]. Chinese Journal of Organic Chemistry, 2023 , 43(1) : 338 -344 . DOI: 10.6023/cjoc202205029
| [1] | Ding, R.; Liu, Y.-G.; Han, M.-R.; Jiao, W.-Y.; Li, J.-Q.; Tian, Y.-H.; Sun, B.-G. J. Org. Chem. 2018, 83, 12939. |
| [2] | Reddy, D.; Fronczek, F. R.; Watkins, E. B. Org. Lett. 2016, 18, 5620. |
| [3] | Reddy, M. D.; Watkins, E. B. J. Org. Chem. 2015, 80, 11447. |
| [4] | Roy, S.; Roy, S.; Gribble, G. W. Tetrahedron 2012, 68, 9867. |
| [5] | Luszczki, J. J.; Swiader, M. J.; Swiader, K.; Paruszewski, R.; Turski, W. A.; Czuczwar, S. J. Fund. Clin. Pharmacol. 2008, 22, 69. |
| [6] | Liu, Q.-C.; Liu, L.-L.; Ranjala, R.; Hendrik, L.; Guo, Y.; Ye, T. Chin. J. Chem. 2020, 38, 1280. |
| [7] | Bode, J. W.; Sohn, S. S. J. Am. Chem. Soc. 2007, 129, 13798. |
| [8] | Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 790. |
| [9] | Malawska, B. Curr. Top. Med. Chem. 2005, 5, 69. |
| [10] | Shaabani, A.; Soleimani, E.; Rezayan, A. H. Tetrahedron Lett. 2007, 48, 6137. |
| [11] | Kobayashi, I.; Muraoka, H.; Hasegawa, M.; Saika, T.; Nishida, M.; Kawamura, M.; Ando, R. J. Antimicrob. Chemother. 2002, 50, 129. |
| [12] | Graul, A.; Castaner, J. Drugs Future 1997, 22, 956. |
| [13] | Merino, O.; Santoyo, B. M.; Montiel, L. E.; Jiménez-Vázquez, H. A.; Zepeda, L. G.; Tamariz, J. Tetrahedron Lett. 2010, 51, 3738. |
| [14] | Najera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584. |
| [15] | Tanaka, H.; Kuroda, A.; Marusawa, H.; Kino, T.; Goto, T.; Hashimoto, M.; Taga, T. J. Am. Chem. Soc. 1987, 109, 5031. |
| [16] | Montalban, A. G.; Boman, E.; Chang, C. D.; Ceide, S. C.; Dahl, R.; Dalesandro, D.; Delaet, N. G. J.; Erb, E.; Ernst, J. T.; Gibbs, A.; Kahl, J.; Kessler, L.; Kucharski, J.; Lum, C.; Lundstroem, J.; Miller, S.; Nakanishi, H.; Roberts, E.; Saiah, E.; Sullivan, R.; Urban, J.; Wang, Z.; Larson, C. J. Bioorg. Med. Chem. Lett. 2010, 20, 4819. |
| [17] | Ghosh, T.; Maity, P.; Ranu, B. J. Org. Chem. 2018, 83, 11758. |
| [18] | He, Z.-Y.; Guo, J.-Y.; Tian, S.-K. Adv. Synth. Catal. 2018, 360, 1544. |
| [19] | Dong, H.; Hou, M.-F. Chin. J. Org. Chem. 2017, 37, 267. (in Chinese) |
| [19] | (董浩, 侯梅芳, 有机化学, 2017, 37, 267.) |
| [20] | Akerbladh, L.; Schembri, L. S.; Larhed, M.; Odell, L. R. J. Org. Chem. 2017, 82, 12520. |
| [21] | Mane, R. S.; Bhanage, B. M. J. Org. Chem. 2016, 81, 1223. |
| [22] | Sasaki, M.; Ando, M.; Kawahata, M.; Yamaguchi, K.; Takeda, K. Org. Lett. 2016, 18, 1598. |
| [23] | Fan, W.-Z.; Shi, D.-Y.; Feng, B.-N. Tetrahedron Lett. 2015, 56, 4638. |
| [24] | Giustiniano, M.; Mercalli, V.; Cassese, H.; Maro, S. D.; Galli, U.; Novellino, E.; Tron, G. C. J. Org. Chem. 2014, 79, 6006. |
| [25] | Wang, Y.-Y.; Liu, Y.-Y. Acta Chim. Sinica 2019, 77, 418. (in Chinese) |
| [25] | (王昱赟, 刘云云, 化学学报, 2019, 77, 418.) |
| [26] | Liu, L.; Du, L.; Zhang, D.-N.; Du, Y.-F.; Zhao, K. Org. Lett. 2014, 16, 5772. |
| [27] | Mupparapu, N.; Khan, S.; Battula, S.; Kushwaha, M.; Gupta, A. P.; Ahmed, Q. N.; Vishwakarma, R. A. Org. Lett. 2014, 16, 1152. |
| [28] | Cunico, R. F.; Chen, J.-X. Synth. Commun. 2003, 33, 1963. |
| [29] | Yao, Y.; Li, W.-T.; Chen, J.-X. Chin. J. Org. Chem. 2014, 34, 2124. (in Chinese) |
| [29] | (姚远, 李伟东, 陈建新, 有机化学, 2014, 34, 2124.) |
| [30] | Yao, Y.; Tong, W.-T.; Chen, J.-X. Mendeleev Commun. 2014, 24, 176. |
| [31] | Chen, X.-J.; Chen, J.-X. Mendeleev Commun. 2013, 23, 106. |
| [32] | Cao, P.; Wen, X.-P.; Chen, J.-X. Synlett 2017, 28, 353. |
| [33] | Li, W.-D.; Han, S.-H.; Liu, Y.-H.; Chen, J.-X. Chin. J. Org. Chem. 2017, 37, 2423. (in Chinese) |
| [33] | (李伟东, 韩生华, 刘艳红, 陈建新, 有机化学, 2017, 37, 2423.) |
| [34] | Zhang, P.-P.; Chen, W.-W.; Feng, H.; Chen, J.-X. Chin. J. Org. Chem. 2019, 39, 3560. (in Chinese) |
| [34] | (张鹏鹏, 陈雯雯, 冯花, 陈建新, 有机化学, 2019, 39, 3560.) |
| [35] | Li, W.-D.; Han, Y.-L.; Chen, J.-X. Tetrahedron 2017, 73, 5813. |
| [36] | Zhang, P.-P.; Han, S.-H.; Chen, J.-X. Chin. J. Org. Chem. 2020, 40, 1737. (in Chinese) |
| [36] | (张鹏鹏, 韩生华, 陈建新, 有机化学, 2020, 40, 1737.) |
| [37] | Liu, H.; Guo, Q.-L.; Chen, J.-X. Tetrahedron Lett. 2015, 56, 5747. |
| [38] | Guo, Q.-L.; Wen, X.-P.; Chen, J.-X. Tetrahedron 2016, 72, 8117. |
| [39] | Han, Y.-L.; Tong, W.-T.; Liu, H.; Chen, J.-X. Chin. J. Org. Chem. 2018, 38, 1993. (in Chinese) |
| [39] | (韩宇玲, 仝文婷, 刘慧, 陈建新, 有机化学, 2018, 38, 1993.) |
| [40] | Guo, Q. L.; Zhao, M. G.; Chen, J. X. Tetrahedron 2020, 76, 131476. |
| [41] | Tong, W.-T.; Cao, P.; Liu, Y.-H.; Chen, J.-X. J. Org. Chem. 2017, 82, 11603. |
| [42] | Wen, X.-P.; Chen, W. W.; Chen, J.-X. Appl.Organometal. Chem. 2019, 33, e5147. |
| [43] | Zhang, W.-J.; Cao, P.; Guo, Q.-L.; Chen, J.-X. Curr. Org. Synth. 2017, 14, 1067. |
| [44] | Zhang, W.- J; Han, S.-H.; Chen, J.-X. Synth. Commun. 2017, 47, 704. |
| [45] | Ma, F.; Liu, H.; Chen, J.-X. Tetrahedron Lett. 2016, 57, 5246. |
| [46] | Han, Y. L.; Li, Y. P.; Han, S.-H.; Chen, J.-X. Synthesis 2019, 51, 2977. |
| [47] | Cunico, R. F.; Motta, A. R. Org. Lett. 2005, 7, 771. |
| [48] | Asahara, H.; Sofue, A.; Kuroda, Y.; Nishiwaki, N. J. Org. Chem. 2018, 83, 13691. |
| [49] | Weiner, B.; Szymanski, W.; Janssen, D. B.; Minnaard, A. J.; Feringa, B. L. Chem. Soc. Rev. 2010, 39, 1656. |
| [50] | Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219. |
| [51] | Lelais, G.; Seebach, D. Biopolymers 2004, 76, 206. |
| [52] | Vicario, J. L.; Badia, D.; Carrillo, L. Org. Lett. 2001, 3, 773. |
| [53] | Liu, Y.-h.; Ha, Y.-L.; Chen, J.-X. Mendeleev Commun. 2021, 31, 128. |
| [54] | Fornicola, R. S.; Oblinger, E.; Montgomery, J. J. Org. Chem. 1998, 63, 3528. |
| [55] | Baichurin, R. I.; Baichurina, L. V.; Aboskalova, N. I.; Berestovitskaya, V. M. Russ. J. Gen. Chem. 2013, 83, 1764. |
| [56] | Cativiela, C.; Ordonez, M.; Viveros-Ceballos, J. L. Tetrahedron 2020, 76, 130875. |
| [57] | Qian, X.-Y.; Xiong, P.; Xu, H.-C. Acta Chim. Sinica 2019, 77, 879. (in Chinese) |
| [57] | (钱向阳, 熊鹏, 徐海超, 化学学报, 2019, 77, 879.) |
| [58] | Han, Y.-Q.; Zhou, T. Chin. J. Chem. 2020, 38, 527. |
| [59] | Schollkopf, U.; Beckhaus, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 293. |
| [60] | Cunico, R. F.; Pandey, R. K. J. Org. Chem. 2005, 70, 9048. |
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