Rh(III)-catalyzed C-H Activation and Annulation via Oxidizing Directing Group. Lei Zhang 03/23/2016 Dong Group
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1 Rh(III)-catalyzed C-H Activation and Annulation via Oxidizing Directing Group Lei Zhang 03/23/2016 Dong Group
2 Content 1 Alkyne involved Annulation in Hua group Brief Introduction of Internal Oxidants Oxidizing Directing Groups Conclusions 2
3 Alkyne involved C H Activation and Annulation in Hua group Guo, B.; Hua, R. J. Org. Chem. 2015, 80, Zheng, L.; Hua, R. Chem. Eur. J. 2014, 20, Zhang, L.; Hua, R. J. Org. Chem. 2014, 79, Zheng, L.; Hua, R. J. Org. Chem. 2014, 79, Zheng, L.; Hua, R. J. Org. Chem. 2012, 77,
4 Indole, Isoquinoline and Heterocycle-Fused Pyridine Synthesis Rhodium(III)-Catalyzed C H Activation via an Auto-Formed and Auto-Cleavable Directing Group Zheng, L.; Ju, J.; Bin, Y.; Hua, R. J. Org. Chem. 2012, 77, Zheng, L.; Hua, R. Chem. Eur. J. 2014, 20,
5 Internal Oxidants Strategies for selective C H functionalization with DGs (a) The strategy of internal oxidant used in C H bond activation (b) (c) Patureau, F. W.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, Huang, H.; Ji, X.; Wu, W.; Jiang, H. Chem. Soc. Rev. 2015, 44, Mo, J.; Wang, L.; Liu, Y.; Cui, X. Synthesis 2015, 47,
6 Oxidizing Directing Groups (DG ox ) The N O Bond as Internal Oxidant Directing Group The N N Bond as Internal Oxidant Directing Group The N S Bond as Internal Oxidant Directing Group The C N Bond as Internal Oxidant Directing Group Huang, H.; Ji, X.; Wu, W.; Jiang, H. Chem. Soc. Rev. 2015, 44, Yu, S.; Lan, Y.; Wan, Bo. and Li, X. J. Am. Chem. Soc. 2015, 137,
7 The N O Bond as Internal Oxidant Directing Group N-oxides as DG ox Oximes as DG ox N-acyloxy group as DG ox N-methoxy/hydroxy group as DG ox Huang, H.; Ji, X.; Wu, W.; Jiang, H. Chem. Soc. Rev. 2015, 44, Mo, J.; Wang, L.; Liu, Y.; Cui, X. Synthesis 2015, 47,
8 The N O Bond as Internal Oxidant Directing Group N-OPiv or N-OBoc group Alkyne-tethered hydroxamic esters as DG ox N-phenoxyacetamide, N-Alkenyloxy amine, O-benzoyl-N,N-diethylhydroxylamine Huang, H.; Ji, X.; Wu, W.; Jiang, H. Chem. Soc. Rev. 2015, 44, Mo, J.; Wang, L.; Liu, Y.; Cui, X. Synthesis 2015, 47,
9 Oximes and its derivatives Chiba Li Too, P. C.; Wang Y.-F.; Chiba S. Org. Lett. 2010, 12, Zhang, X.; Chen, D.; Zhao, M.; Zhao J.; Jia, A.; Li, X. Adv. Synth. Catal. 2011, 353,
10 Formation of pyridines by the use of α,β-unsaturated oximines Too, P. C.; Noji, T.; Lim, Y. J.; Li, X.; Chiba, S. Synlett 2011, Hyster, T. K.; Rovis, T. Chem. Commun. 2011, 47,
11 Mechanism discuss on C H activation of oximines with alkynes 11
12 Formation of Pyridines by the Cyclization of α,β-unsaturated Oximines with Alkenes Neely, J. M.; Rovis, T. J. Am. Chem. Soc. 2013, 135,
13 Formation of pyridines using acrylic acids Neely, J. M.; Rovis, T. J. Am. Chem. Soc. 2014, 136,
14 One-pot synthesis of isoquinolines Zheng, L.; Ju, J.; Bin, Y.; Hua, R. J. Org. Chem. 2012, 77,
15 Rhodium catalyzed coupling of oximine esters with 1,3-dienes for the synthesis of isoquinolones Zhao, D.; Lied, F.; Glorius, F. Chem. Sci. 2014, 5,
16 Proposed mechanism Zhao, D.; Lied, F.; Glorius, F. Chem. Sci. 2014, 5,
17 N-hydroxylamine and its derivatives Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010,132, Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, Xu, L.; Zhu, Q.; Huang, G.; Cheng, B.; Xia, Y. J. Org. Chem. 2012, 77,
18 Rhodium(III)-Catalyzed Heterocycle Synthesis Using Terminal Alkyne and Alkene Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133,
19 Rhodium catalyzed C H functionalization between derevatives of N-hydroxybenzamide and alkenes Switching reaction pathway through different oxidizing directing groups Rakshit, S.; Grohmann, C.; Glorius, F. J. Am. Chem. Soc. 2011, 133,
20 Rhodium(III)-Catalyzed Intramolecular Annulation Xu, X.; Liu, Y.; Park, C.-M. Angew. Chem., Int. Ed. 2012, 124, Davis, T. A.; Hyster, T. K.; Rovis T. Angew. Chem., Int. Ed. 2013, 52,
21 Synthesis of Diverse Bisheterocycles of 1,3-Diyne Yu, D.-G.; Gensch, T.; Glorius, F. Angew. Chem., Int. Ed. 2014, 53,
22 Rh(III)-Catalyzed C H Activation and Annulation with Alkyne MIDA Boronates Wang, H.; Glorius, F. J. Am. Chem. Soc. 2012, 134, Presset, M.; Molander, G. A. Org. Lett. 2013, 15,
23 Rh(III)-Catalyzed C H Activation for the Regioselective Synthesis of Naphthyridinones Huckins, J. R.; Hwang, T.-L.; Bio, M. M. J. Am. Chem. Soc. 2013, 135,
24 Rh(III)-Catalyzed Cyclization of Benzamides and 1,6-Enynes Fukui, Y.; Tian, P.; Lin, G.-Q. J. Am. Chem. Soc. 2014, 136,
25 Rhodium(III)-Catalyzed C H Activation and intermolecular Annulation with Allenes Wang, H.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51,
26 Formation of Trisubstituted Allenes Using Allenylsilanes Zeng, R.; Wu, S.; Fu, C. L.; Ma, S. J. Am. Chem. Soc. 2013, 135,
27 Rh(III)-Catalyzed Coupling of Benzamides and Diazo Compounds Hyster, T. K.; Ruhl, K. E.; Rovis, T. J. Am. Chem. Soc. 2013, 135, Cui, S.; Zhang, Y; Wang, D.; Wu, Q. Chem. Sci. 2013, 4,
28 Synthesis of Isoquinolones from Amides and Cyclopropenes Hyster, T. K.; Rovis, T. Synlett 2013,
29 Rh(III)-catalyzed C H Activation/Cycloaddition of Benzamides and Methylenecyclopropanes Cui, S.; Zhang, Y.; Wu, Q. Chem. Sci. 2013, 4,
30 Proposed Mechanism A D C B Cui, S.; Zhang, Y.; Wu, Q. Chem. Sci. 2013, 4,
31 Rh(III)-Catalyzed C H Activation/Cyclization of Indoles and Pyrroles Zhang, Y.; Zheng, J.; Cui, S. J. Org. Chem. 2014, 79,
32 Proposed Mechanism Zhang, Y.; Zheng, J.; Cui, S. J. Org. Chem. 2014, 79,
33 Rhodium catalyzed coupling between N-phenoxyamides and cyclopropenes Zhang, H.; Wang, J. Angew. Chem., Int. Ed. 2014, 53,
34 Rh(III)-Catalyzed Cyclopropanation Initiated by C H Activation Piou, T.; Rovis, T. J. Am. Chem. Soc. 2014, 136,
35 Rhodium catalyzed cyclization of O-benzoyl-N,Ndiethylhydroxylamine with alkynes Li, X. G.; Liu, K.; Zou, G.; Liu, P. N. Adv. Synth. Catal. 2014, 356,
36 The N N Bond as Internal Oxidant Directing Group Liu, B.; Song, C.; Sun, C.; Zhou, S.; Zhu, J. J. Am. Chem. Soc. 2013, 135, Wang, C.; Huang, Y. Org. Lett. 2013, 15,
37 Synthesis of Indoles Using N N Bond as the Internal Oxidant Zhao, D.; Shi, Z.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, Zheng, L.; Hua, R. Chem. Eur. J. 2014, 20, Muralirajana, K.; Cheng, C. H. Adv. Synth. Catal. 2014, 356,
38 Proposed reaction mechanism for the indole synthesis from hydrazine Zhao, D.; Shi, Z.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52,
39 Rhodium(III)-catalyzed the formation of isoquinolines using hydrazine as an oxidizing directing group Chuang, S.-C.; Gandeepan, P.; Cheng, C.-H. Org. Lett. 2013, 15,
40 The N S Bond as Internal Oxidant Directing Group Zhang, Q.-R.; Huang, J.-R.; Zhang, W.; Dong, L. Org. Lett. 2014, 16,
41 The C N Bond as Internal Oxidant Directing Group Rhodium-Catalyzed C H Activation of Phenacyltriethylammonium Yu, S.; Liu, S.; Lan, Y.; Wan, B.; Li, X. J. Am. Chem. Soc. 2015, 137,
42 Conclusions The internal oxidant strategy has emerged as a powerful tool in metal-catalyzed direct C-H activation reactions; As direction group: improve the reactivity and selectivity of C- H functionalization, broaden the substrate scope and decreasing the amount of waste formation; Further development focus on finding new types of internal oxidants and improving the mechanistic understanding. 43
43 THANK YOU FOR YOUR ATTENTION! 44
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