Chemstation小编继续为学习有机化学的各位同行带来Fukuyama-Yokoshima研究组反应机理问题的详细解答的第二十期。

问题 1

基本文献

[1] D. J. Jansen, R. A. Shenvi, J. Am. Chem. Soc. 2013, 135, 1209. doi: 10.1021/ja310778t .

反应机理

参考文献

[1] R. T. La Londe, R. A. Florence, B. A. Horenstein, R. C. Fritz, L. Silveira, J. Clardy, B. S. Krishnan, J. Org. Chem.1985, 50, 85. doi: 10.1021/jo00201a017 .

[2] D. Del Mazza, M. G. Reinecke, J. Org. Chem. 1981, 46, 128. doi: 10.1021/jo00314a028 .

问题 2

基本文献

[1] S. Jansone-Popova, J. A. May, J. Am. Chem. Soc. 2012, 134, 17877. doi: 10.1021/ja308305z .

反应机理

参考文献

[1] S. Jansone-Popova, J. A. May, J. Am. Chem. Soc. 2012, 134, 17877. doi: 10.1021/ja308305z .

问题 3

基本文献

[1] X. Sun, Z. Wu, W. Qi, X. Ji, C. Cheng, Y. Zhang, Org. Lett. 2019, 21, 6508. doi: 10.1021/acs.orglett.9b02386 .

反应机理

参考文献

[1] Y. Zhu, R. G. Cornwall, H. Du, B. Zhao, Y. Shi, Acc. Chem. Res. 2014, 47, 3665. doi: 10.1021/ar500344t .

[2] F. Cardona, A. Goti, Nature Chem . 2009, 1 ,269. doi: 10.1038/nchem.256 .

[3] A. J. Rago, G. Dong, Green Synth . Catal . 2021, in press. doi: 10.1016/j.gresc.2021.02.001 .

[4] Y. Zheng, Y. Zhu, Y. Shi, Angew. Chem. Int. Ed. 2014, 53, 11280. doi: 10.1002/anie.201405365 .

[5] B. Zhou, Z. Wu, D. Ma, X. Ji, Y. Zhang, Org. Lett. 2018, 20, 6440. doi: 10.1021/acs.orglett.8b02750 .

[6] T. A. Ramirez, Q. Wang, Y. Zhu, H. Zheng, X. Peng, R. G. Cornwall, Y. Shi, Org. Lett. 2013, 15, 4210. doi: 10.1021/ol401935c .

[7] Y. Wen, B. Zhao, Y. Shi, Org. Lett. 2009, 11, 2365. doi: 10.1021/ol900808z .

[8] H. Du, W. Yuan, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2007, 129, 7496. doi: 10.1021/ja072080d .

[9] H. Du, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2008, 130, 8590. doi: 10.1021/ja8027394 .

[10] Y. Zhu, Y. Shi, Chem.-Eur. J. 2014, 20, 13901. doi: 10.1002/chem.201404381 .

[11] H. Du, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2007, 129, 762. doi: 10.1021/ja0680562 .

[12] L. Xu, H. Du, Y. Shi, J. Org. Chem. 2007, 72, 7038. doi: 10.1021/jo0709394 .

[13] H. Du, W. Yuan, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2007, 129, 11688. doi: 10.1021/ja074698t .

[14] L. Xu, Y. Shi, J. Org. Chem. 2008, 73, 749. doi: 10.1021/jo702167u .

[15] W. Yuan, H. Du, B. Zhao, Y. Shi, Org. Lett. 2007, 9, 2589. doi: 10.1021/ol071105a .

[16] Q. Dai, B. Zhao, Y. Yang, Y. Shi, Org. Lett. 2019, 21, 5157. doi: 10.1021/acs.orglett.9b01762 .

[17] S. Debnath, L. Liang, M. Lu, Y. Shi, O rg. Lett. 2021, 23, 3237. doi: 10.1021/acs.orglett.1c00466 .

[18] L. Zhang, J. Chen, T. Zhong, X. Zheng, J. Zhou, X. Jiang, C. Yu, J. Org. Chem. 2020, 85, 10823. doi: 10.1021/acs.joc.0c01365 .

[19] Y. Zhu, Y. Shi, Org. Biomol. Chem. 2013, 11 ,7451. doi: 10.1039/C3OB41621F .

[20] J. Li, J. Chen, L. Wang, Y. Shi, Org. Lett. 2021, 23, 3646. doi: 10.1021/acs.orglett.1c01043 .

[21] C. Shao, B. Zhou, Z. Wu, X. Ji, Y. Zhang, Adv. Synth. Catal. 2018, 360, 887. doi: 10.1002/adsc.201701039 .

[22] D. Ma, X. Ji, Z. Wu, C. Cheng, B. Zhou, Y. Zhang, Adv. Synth. Catal. 2019, 361, 739. doi: 10.1002/adsc.201801367 .

[23] W. Han, Y. Yang, Y. Zhu, Y. Shi, Org. Biomol. Chem. 2019, 17, 6998. doi: 10.1039/C9OB00901A .

[24] B. Zhao, H. Du, Y. Shi, J. Am. Chem. Soc. 2008, 130, 7220. doi: 10.1021/ja802242h .

[25] J. Song, J. Zhang, S. Chen, T. Fan, L. Gong, J. Am. Chem. Soc. 2018, 140, 3177. doi: 10.1021/jacs.7b12628 .

[26] Y. Zhu, Y. Shi, Org. Lett. 2013, 15, 1942. doi: 10.1021/ol4005917 .

[27] Y. Zhu, T. Xiong, W. Han, Y. Shi, Org. Lett. 2014, 16, 6144. doi: 10.1021/ol5030103 .

[28] Y. Zhu, B. Zhao, Y. Shi, Org. Lett. 2013, 15, 992. doi: 10.1021/ol303431h .

[29] M. Komatsu, S. Tamabuchi, S. Minakata, Y. Ohshiro, Heterocycles 1999, 50, 67. doi: 10.3987/COM-98-S(H)45.

[30] T. A. Ramirez, B. Zhao, Y. Shi, Tetrahedron Lett. 2010, 51, 1822. doi: 10.1016/j.tetlet.2010.01.114 .

[31] B. Zhao, H. Du, S. Cui, Y. Shi, J. Am. Chem. Soc. 2010, 132, 3523. doi: 10.1021/ja909459h .

[32] G. Bocelli, M. Catellani, F. Cugini, R. Ferraccioli, Tetrahedron Lett. 1999, 40, 2623. doi: 10.1016/S0040-4039(99)00232-4 .

[33] F. Paul, J. Fischer, P. Ochsenbein, J. A. Osborn, C. R. Chimie 2002, 5, 267. doi: 10.1016/S1631-0748(02)01378-4 .

[34] K. A. Abboud, L. A. Villanueva, J. M. Boncella, Acta Crystallogr. 1993, C49, 1848. doi: 10.1107/S0108270193002343 .

[35] H. Thu, W. Yu, C Che, J. Am. Chem. Soc. 2006, 128, 9048. doi: 10.1021/ja062856v .

[36] G. Besenyei, L. Párkányi, I. Foch, L. I. Simándi, Angew. Chem. Int. Ed. 2000, 39, 956. doi: 10.1002/(SICI)1521-3773(20000303)39:5<956::AID-ANIE956>3.0.CO;2-6 .

[37] I. I. Moiseev, T. A. Stromnova, M. N. Vargaftik, S. T. Orlova, T. V. Chernysheva, I. P. Stoloarv, Catal. Today 1999, 51, 595. doi: 10.1016/S0920-5861(99)00043-7 .