Substrate-Directed Catalytic Asymmetric Hydroalkynylation of Alkenes
- Corresponding author: Li Bijie, bijieli@mail.tsinghua.edu.cn
Citation:
Zhang Wenwen, Wang Zixuan, Bai Xiaoyan, Li Bijie. Substrate-Directed Catalytic Asymmetric Hydroalkynylation of Alkenes[J]. Chinese Journal of Organic Chemistry,
;2020, 40(5): 1087-1095.
doi:
10.6023/cjoc202002017
Wang, J. Stereoselective Alkene Synthesis; Springer-Verlag, Berlin/Heidelberg, 2012.
(a) Coombs, J. R.; Morken, J. P. Angew. Chem. Int. Ed. 2016, 55, 2636.
(b) Chen, J. H.; Lu, Z. Org. Chem. Front. 2018, 5, 260.
(c) Dhungana, R. K.; Kc, S.; Basnet, P.; Giri, R. Chem. Rec. 2018, 18, 1314.
(d) Zhang, J.-S.; Liu, L.; Chen, T.; Han, L.-B. Chem. Asian J. 2018, 13, 2277.
(e) Ping, Y.; Li, Y.; Zhu, J.; Kong, W. Angew. Chem., Int. Ed. 2019, 58, 1562.
(f) Li, S.; Li, Z.; You, C.; Lü, H.; Zhang, X. Chin. J. Org. Chem. 2019, 39, 1568.
(g) Cheng, L.; Xie, J. Chin. J. Org. Chem. 2020, 40, 247.
(h) Zhou, Q.; Feng, X, ; Yang, J.; Du, H. Chin. J. Org. Chem. 2019, 39, 2188.
Wang, Z.-X.; Bai, X.-Y.; Li, B.-J. Chin. J. Chem. 2019, 37, 1174.
(a) Knöpfel, T. F.; Zarotti, P.; Ichikawa, T.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 9682.
(b) Nishimura, T.; Guo, X.-X.; Uchiyama, N.; Katoh, T.; Hayashi, T. J. Am. Chem. Soc. 2008, 130, 1576.
(c) Yazaki, R.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 10275.
(d) Shirakura, M.; Suginome, M. Angew. Chem. Int. Ed. 2010, 49, 3827.
(e) Fan, B.-M.; Yang, Q.-J.; Hu, J.; Fan, C.-L.; Li, S.-F.; Yu, L.; Huang, C.; Tsang, W. W.; Kwong, F. Y. Angew. Chem., Int. Ed. 2012, 51, 7821.
(f) Sawano, T.; Ou, K.; Nishimura, T.; Hayashi, T. Chem. Commun. 2012, 48, 6106.
(g) Blay, G.; Pedro, J. R.; Sanz-Marco, A. Synthesis 2018, 50, 3281.
(h) Zhi, Y.; Huang, J.; Liu, N.; Lu, T.; Dou, X. Org. Lett. 2017, 19, 2378.
(a) Fu, L.; Zhou, S.; Wan, X.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2018, 140, 10965.
(b) Yeqiang, H.; Ding, Y.; Zhou, T.; Yan, S.-Y.; Song, H.; Shi, B.-F. J. Am. Chem. Soc. 2019, 141, 4558.
(c) Dong, X.-Y.; Zhang, Y.-F.; Ma, C.-L.; Gu, Q.-S.; Wang, F.-L.; Li, Z.-L.; Jiang, S.-P.; Liu, X.-Y. Nat. Chem. 2019, 11, 1158.
(d) Chen, Q.; Tang, Y.; Huang, sT.; Liu, X.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2016, 55, 5286.
(a) Trost, B. M., Li, C.-J. Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations, Wiley, New York, 2014.
(b) Li, Y.; Liu, X.; Jiang, H.; Liu, B.; Chen, Z.; Zhou, P. Angew. Chem., Int. Ed. 2011, 50, 6341.
(c) Sivaguru, P.; Wang, Z.; Zanoni, G.; Bi, X. Chem. Soc. Rev. 2019, 48, 2615.
(d) Hong, F.-L.; Wang, Z.-S.; Wei, D.-D.; Zhai, T.-Y.; Deng, G.-C.; Lu, X.; Liu, R.-S.; Ye, L.-W. J. Am. Chem. Soc. 2019, 141, 16961.
(e) Zhu, D.; Chen, L.; Zhang, H.; Ma, Z.; Jiang, H.; Zhu, S. Angew. Chem., Int. Ed. 2018, 57, 12405.
(f) Ren, R.; Wu, Z.; Xu, Y.; Zhu, C. Angew. Chem., Int. Ed. 2016, 55, 2866.
(g) Shen, T.; Wang, T.; Qin, C.; Jiao, N. Angew. Chem., Int. Ed. 2013, 52, 6677.
(h) Xu, G.; Zhao, H.; Fu, B.; Cang, A.; Zhang, G.; Zhang, Q.; Xiong, T.; Zhang, Q. Angew. Chem., Int. Ed. 2017, 56, 13130. (i) Wang, Q.; Yu, X.; Jin, J.; Wu, Y.; Liang, Y. Chin. J. Chem. 2018, 36, 223. (j) Jiang, Z.; Lu, P.; Wang, Y. Org. Lett. 2012, 14, 6266.
(k) Zhu, C.; Chu, H.; Li, G.; Ma, S.; Zhang, J. J. Am. Chem. Soc. 2019, 141, 19246.
Diederich, F.; Stang, P. J.; Tykwinski, R. R. Acetylene Chemistry, Wiley-VCH, Weinheim, 2005.
(a) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1959, 81, 4256.
(b) Winstein, S.; Sonnenberg, J.; De Vries, L. J. Am. Chem. Soc. 1959, 81, 6523.
(c) Winstein, S.; Sonnenberg, J. J. Am. Chem. Soc. 1961, 83, 3235.
(a) Thompson, H. W.; McPherson, E. J. Am. Chem. Soc. 1974, 96, 6232.
(b) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986, 51, 2655.
(a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
(b) Zhu, S.-F.; Zhou, Q.-L. Acc. Chem. Res. 2017, 50, 988.
(a) Evans, D. A.; Fu, G. C. J. Am. Chem. Soc. 1991, 113, 4042.
(b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198.
(c) Bochat, A. J.; Shoba, V. M.; Takacs, J. M. Angew. Chem., Int. Ed. 2019, 58, 9434.
Kawasaki, Y.; Ishikawa, Y.; Igawa, K.; Tomooka, K. J. Am. Chem. Soc. 2011, 133, 20712.
(a) Willis, M. C. Chem. Rev. 2010, 110, 725.
(b) Murphy, S. K.; Bruch, A.; Dong, V. M. Angew. Chem., Int. Ed. 2014, 53, 2455.
(a) Albrecht, M. Chem. Rev. 2010, 110, 576.
(b) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
(c) He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J.-Q. Chem. Rev. 2017, 117, 8754.
(d) Li, B.-J.; Shi, Z.-J. Chem. Soc. Rev. 2012, 41, 5588.
Wang, M.-X. Chem. Commun. 2015, 51, 6039.
doi: 10.1039/C4CC10327K
(a) Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667.
(b) Gooßen, L. J.; Rauhaus, J. E.; Deng, G. Angew. Chem., Int. Ed. 2005, 44, 4042.
Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510.
Sakaki, S.; Sumimoto, M.; Fukuhara, M.; Sugimoto, M.; Fujimoto, H.; Matsuzaki, S. Organometallics 2002, 21, 3788.
Bai, X. Y.; Zhang, W. W.; Li, Q.; Li, B.-J. J. Am. Chem. Soc. 2018, 140, 506.
doi: 10.1021/jacs.7b12054
Peshkov, V. A.; Pereshivko, O. P.; Van der Eycken, E. V. Chem. Soc. Rev. 2012, 41, 3790.
doi: 10.1039/c2cs15356d
Hartwig, J. F. Organotransition Metal Chemistry:From Bonding to Catalysis, University Science Books, Sausalito, CA, 2010.
Bai, X.-Y.; Wang, Z.-X.; Li, B.-J. Angew. Chem., Int. Ed. 2016, 55, 9007.
doi: 10.1002/anie.201601792
Yu, Z.; Meng, L.; Lin, Z. Organometallics 2019, 38, 2998.
doi: 10.1021/acs.organomet.9b00343
Rössler, S. L.; Petrone, D. A.; Carreira, E. M. Acc. Chem. Res. 2019, 52, 2657.
Zhang, W.-W.; Zhang, S.-L.; Li, B.-J. Angew. Chem., Int. Ed. 2020, 59, 6874.
doi: 10.1002/anie.201916088
(a) Krautwald, S.; Carreira, E. M. J. Am. Chem. Soc. 2017, 139, 5627.
(b) Huo, X.; He, R.; Zhang, X.; Zhang, W. J. Am. Chem. Soc. 2016, 138, 11093.
(c) Wei, L.; Zhu, Q.; Xu, S.-M.; Chang, X.; Wang, C.-J. J. Am. Chem. Soc. 2018, 140, 1508.
(d) Zhang, Q.; Yu, H.; Shen, L.; Tang, T.; Dong, D.; Chai, W.; Zi, W. J. Am. Chem. Soc. 2019, 141, 14554.
(a) Mei, T.-S.; Patel, H. H.; Sigman, M. S. Nature 2014, 508, 340.
(b) Liu, W.-B.; Okamoto, N.; Alexy, E. J.; Hong, A. Y.; Tran, K.; Stoltz, B. M. J. Am. Chem. Soc. 2016, 138, 5234.
(c) Guo, C.; Fleige, M.; Janssen-Muller, D.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2016, 138, 7840.
Wang, Z.-X.; Bai, X.-Y.; Yao, H.-C.; Li, B.-J. J. Am. Chem. Soc. 2016, 138, 14872.
Li, Y.; Wu, D.; Cheng, H.-G.; Yin, G. Angew. Chem., Int. Ed. 2020, 59, 7990.
(a) Quasdorf, K. W.; Overman, L. E. Nature 2014, 516, 181.
(b) Feng, J.; Holmes, M.; Krische, M. J. Chem. Rev. 2017, 117, 12564.
(c) Zeng, X.-P.; Cao, Z.-Y.; Wang, Y.-H.; Zhou, F.; Zhou, J. Chem. Rev. 2016, 116, 7330.
Wang, Z.-X.; Li, B.-J. J. Am. Chem. Soc. 2019, 141, 9312.
doi: 10.1021/jacs.9b03027
(a) Wang, H.; Bai, Z.; Jiao, T.; Deng, Z.; Tong, H.; He, G.; Peng, Q.; Chen, G. J. Am. Chem. Soc. 2018, 140, 3542.
(b) Liu, Z.; Li, X.; Zeng, T.; Engle, K. M. ACS Catal. 2019, 3260.
(c) Shen, H.-C.; Zhang, L.; Chen, S.-S.; Feng, J.; Zhang, B.-W.; Zhang, Y.; Zhang, X.; Wu, Y.-D.; Gong, L.-Z. ACS Catal. 2019, 9, 791.
(d) Nimmagadda, S. K.; Liu, M.; Karunananda, M. K.; Gao, D. W.; Apolinar, O.; Chen, J. S.; Liu, P.; Engle, K. M. Angew. Chem., Int. Ed. 2019, 58, 3923.
(e) Vanable, E. P.; Kennemur, J. L.; Joyce, L. A.; Ruck, R. T.; Schultz, D. M.; Hull, K. L. J. Am. Chem. Soc. 2019, 141, 739.
(f) Tang, C.; Zhang, R.; Zhu, B.; Fu, J.; Deng, Y.; Tian, L.; Guan, W.; Bi, X. J. Am. Chem. Soc. 2018, 140, 16929.
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