多功能氧酰胺导向基在碳氢键活化反应中的研究进展

doi:10.3866/PKU.WHXB201812016

Abstract

Abstract:

Transition-metal-catalyzed C―H functionalization reactions, assisted by directing groups (DGs), have become some of the most powerful strategies to form C―C and C―X (X = O, N, S, etc.) bonds. It has brought about a revolution in the synthesis of drugs and natural products, and the method is widely applicable in the fields of material chemistry and pharmaceutical industry. This strategy has mainly focused on regioselective C―H functionalization of amides, esters, carbamates, and enamides with DGs to form C―C and C―X bonds. Since these DGs are relatively stable, they must be removed by other methods when the reaction is completed. Therefore, the use of a traceless DG is one of the important challenges for transition-metal-catalyzed C―H functionalization. Recently, N-phenoxyamide has been attracting significant research attention as a versatile DG. Oxyacetamide (O―NHAc) is one of the most versatile functionalities for directed C―H functionalization cascades, such as the internal oxidation with N―O bond cleavage. The O―NHAc has been reported as a superb DG for redox-neutral C―H activation/annulation cascade reactions to synthesize phenol and complex heterocyclic scaffolds by coupling with alkynes, alkenes, heteroarenes, and diazo compounds. However, for the external oxidation with preservation of the N―O bond, e.g. when a stoichiometric external oxidant is present, N-phenoxyamides could react with aldehydes or α, β-unsaturated aldehydes. In addition, the solvent can control the chemoselectivity. In this minireview, the C―H bond functionalization of N-phenoxyamide is divided into five categories according to the different substrates, viz. alkenes, alkynes, diazo, and other compounds and intramolecular C―H bond activation reactions. Based on experimental and theoretical research results, the reaction mechanism was discussed. In the first part, we summarize the ortho-alkylation, alkenylation, and cyclization of N-phenoxyamide with olefins. In the second part, we present the Rh- and Ir-catalyzed C―H activation or cyclization of N-phenoxyamide with alkanes to synthesize phenol or benzofuran compounds. In the third part, we describe the synthesis of phenolic compounds functionalized by Rh-catalyzed diazo compounds by carbene intermediates and N-phenoxyamides. The forth part summarizes the C―H activation/annulation reaction using aldehydes, heterocyclic aromatic, and sulfur reagents as substrates. The last part of the paper generalizes the intramolecular ortho-hydroxylation and ortho, para-amidation reactions.

Key words: C―H activation, N-phenoxyamides, Multitasking, Phenols, Selenium

MSC2000:

O643

Yuelu ZHU,Xinyang ZHAO,Qian WU,Ying CHEN,Jing ZHAO. Research Advances in C―H Bond Activation of Multitasking N-Phenoxyamides[J].Acta Physico-Chimica Sinica, 2019, 35(9): 989-1004.

Figures/Tables 38

Fig 1

Fig 2

Fig 3

Fig 4

Fig 5

Fig 6

Fig 7

Fig 8

Fig 9

Fig 10

Fig 11

Fig 12

Fig 13

Fig 14

Fig 15

Fig 16

Fig 17

Fig 18

Fig 19

Fig 20

Fig 21

Fig 22

Fig 23

Fig 24

Fig 25

Fig 26

Fig 27

Fig 28

Fig 29

Fig 30

Fig 31

Fig 32

Fig 33

Fig 34

Fig 35

Fig 36

Fig 37

Fig 38

References 77

1	Gutekunst W. R. ; Baran P. S. Chem. Soc. Rev. 2011, 40, 1976. doi: 10.1039/C0CS00182A
2	Wencel-Delord J. ; Droge T. ; Liu F. ; Glorius F. Chem. Soc. Rev. 2011, 40, 4740. doi: 10.1039/C1CS15083A
3	Arockiam P. B. ; Bruneau C. ; Dixneuf P. H. Chem. Rev. 2012, 112, 5879. doi: 10.1021/cr300153j
4	Li B. J. ; Shi Z. J. Chem. Soc. Rev. 2012, 41, 5588. doi: 10.1039/C2CS35096C
5	Liu C. ; Yuan J. ; Gao M. ; Tang S. ; Li W. ; Shi R. ; Lei A. Chem. Rev. 2015, 115, 12138. doi: 10.1021/cr500431s
6	He J. ; Wasa M. ; Chan K. S. L. ; Shao Q. ; Yu J. Q. Chem. Rev. 2017, 117, 8754. doi: 10.1021/acs.chemrev.6b00622
7	Park Y. ; Kim Y. ; Chang S. Chem. Rev. 2017, 117, 9247. doi: 10.1021/acs.chemrev.6b00644
8	Yi H. ; Zhang G. ; Wang H. ; Huang Z. ; Wang J. ; Singh A. K. ; Lei A. Chem. Rev. 2017, 117, 9016. doi: 10.1021/acs.chemrev.6b00620
9	Guo X. X. ; Gu D. W. ; Wu Z. ; Zhang W. Chem. Rev. 2015, 115, 1622. doi: 10.1021/cr500410y
10	Liu J. ; Chen G. ; Tan Z. Adv. Synth. Catal. 2016, 358, 1174. doi: 10.1002/adsc.201600031
11	Wendlandt A. E. ; Suess A. M. ; Stahl S. S. Angew. Chem. Int. Edit. 2011, 50, 11062. doi: 10.1002/anie.201103945
12	Abrams D. J. ; Provencher P. A. ; Sorensen E. J. Chem. Soc. Rev. 2018, 47, 8925. doi: 10.1039/c8cs00716k
13	Jayakumar J. ; Parthasarathy K. ; Chen Y. H. ; Lee T. H. ; Chuang S. C. ; Cheng C. H. Angew. Chem. Int. Edit. 2014, 53, 9889. doi: 10.1002/anie.201405183
14	Shan G. ; Flegel J. ; Li H. ; Merten C. ; Ziegler S. ; Antonchick A. P. ; Waldmann H. Angew. Chem. Int. Edit. 2018, 57, 14250. doi: 10.1002/anie.201809680
15	Yang W. ; Dong J. ; Wang J. ; Xu X. Org. Lett. 2017, 19, 616. doi: 10.1021/acs.orglett.6b03777
16	Wu J. Q. ; Zhang S. S. ; Gao H. ; Qi Z. ; Zhou C. J. ; Ji W. W. ; Liu Y. ; Chen Y. ; Li Q. ; Li X. ; et al J. Am. Chem. Soc. 2017, 139, 3537. doi: 10.1021/jacs.7b00118
17	Wang H. W. ; Lu Y. ; Zhang B. ; He J. ; Xu H. J. ; Kang Y. S. ; Sun W. Y. ; Yu J. Q. Angew. Chem. Int. Edit. 2017, 56, 7449. doi: 10.1002/anie.201703300
18	Wang C. Q. ; Zhang Y. ; Feng C. Angew. Chem. Int. Edit. 2017, 56, 14918. doi: 10.1002/anie.201708505
19	Wang C. Q. ; Ye L. ; Feng C. ; Loh T. P. J. Am. Chem. Soc. 2017, 139, 1762. doi: 10.1021/jacs.6b12142
20	Tan E. ; Quinonero O. ; Elena de Orbe M. ; Echavarren A. M. ACS Catal. 2018, 8, 2166. doi: 10.1021/acscatal.7b04395
21	Hua Y. ; Asgari P. ; Avullala T. ; Jeon J. J. Am. Chem. Soc. 2016, 138, 7982. doi: 10.1021/jacs.6b04018
22	Wu Y. ; Li W. ; Jiang L. ; Zhang L. ; Lan J. ; You J. Chem. Sci. 2018, 9, 6878. doi: 10.1039/C8SC02529K
23	Lv S. ; Li Y. ; Yao T. ; Yu X. ; Zhang C. ; Hai L. ; Wu Y. Org. Lett. 2018, 20, 4994. doi: 10.1021/acs.orglett.8b01952
24	Zhou X. ; Pan Y. ; Li X. Angew. Chem. Int. Edit. 2017, 56, 8163. doi: 10.1002/anie.201704036
25	Barday M. ; Janot C. ; Halcovitch N. R. ; Muir J. ; Aissa C. Angew. Chem. Int. Edit. 2017, 56, 13117. doi: 10.1002/anie.201706804
26	Wang F. ; Yu X. ; Qi Z. ; Li X. Chem. Eur. J. 2016, 22, 511. doi: 10.1002/chem.201504179
27	Tian M. ; Liu B. ; Sun J. ; Li X. Org. Lett. 2018, 20, 4946. doi: 10.1021/acs.orglett.8b02078
28	Li J. ; Zhang Z. ; Tang M. ; Zhang X. ; Jin J. Org. Lett. 2016, 18, 3898. doi: 10.1021/acs.orglett.6b01916
29	Shen Y. ; Liu G. ; Zhi Z. ; Lu X. Org. Lett. 2013, 15, 3366. doi: 10.1021/ol4014188
30	Xu L. ; Zhu Q. ; Huang G. ; Cheng B. ; Xia Y. J. Org. Chem. 2012, 77, 3017. doi: 10.1021/jo202431q
31	Liu B. ; Fan Y. ; Gao Y. ; Sun C. ; Xu C. ; Zhu J. J. Am. Chem. Soc. 2013, 135, 468. doi: 10.1021/ja3099245
32	Hyster T. K. ; Ruhl K. E. ; Rovis T. J. Am. Chem. Soc. 2013, 135, 5364. doi: 10.1021/ja402274g
33	Duan P. ; Lan X. ; Chen Y. ; Qian S. S. ; Li J. J. ; Lu L. ; Lu Y. ; Chen B. ; Hong M. ; Zhao J. Chem. Commun. 2014, 50, 12135. doi: 10.1039/C4CC05485G
34	Zhang H. ; Wang K. ; Wang B. ; Yi H. ; Hu F. ; Li C. ; Zhang Y. ; Wang J. Angew. Chem. Int. Edit. 2014, 53, 13234. doi: 10.1002/anie.201408555
35	Prakash S. ; Muralirajan K. ; Cheng C. H. Chem. Commun. 2015, 51, 13362. doi: 10.1039/C5CC04211A
36	Hu Z. ; Tong X. ; Liu G. Org. Lett. 2016, 18, 1702. doi: 10.1021/acs.orglett.6b00616
37	García M. P. ; Oro L. A. ; Lahoz F. J. Angew. Chem. Int. Edit. 1988, 27, 1700. doi: 10.1002/anie.198817001
38	Haynes A. ; Mann B. E. ; Morris G. E. ; Maitlis P. M. J. Am. Chem. Soc. 1993, 115, 4093. doi: 10.1021/ja00063a030
39	Lerchen A. ; Knecht T. ; Daniliuc C. G. ; Glorius F. Angew. Chem. Int. Edit. 2016, 55, 15166. doi: 10.1002/anie.201608729
40	Wang X. ; Lerchen A. ; Gensch T. ; Knecht T. ; Daniliuc C. G. ; Glorius F. Angew. Chem. Int. Edit. 2017, 56, 1381. doi: 10.1002/anie.201610117
41	Shin K. ; Kim H. ; Chang S. Acc. Chem. Res. 2015, 48, 1040. doi: 10.1021/acs.accounts.5b00020
42	Yu S. ; Liu S. ; Lan Y. ; Wan B. ; Li X. J. Am. Chem. Soc. 2015, 137, 1623. doi: 10.1021/ja511796h
43	Park Y. ; Heo J. ; Baik M. H. ; Chang S. J. Am. Chem. Soc. 2016, 138, 14020. doi: 10.1021/jacs.6b08211
44	Yang Y. F. ; Houk K. N. ; Wu Y. D. J. Am. Chem. Soc. 2016, 138, 6861. doi: 10.1021/jacs.6b03424
45	Li Y. ; Tang Y. ; He X. ; Shi D. ; Wu J. ; Xu S. Chem. Eur. J. 2017, 23, 7453. doi: 10.1002/chem.201701703
46	Wang Y. ; Chen Y. ; Yang Y. ; Zhou B. Org. Chem. Front. 2018, 5, 1844. doi: 10.1039/C8QO00265G
47	Wang X. ; Lerchen A. ; Daniliuc C. G. ; Glorius F. Angew. Chem. Int. Edit. 2018, 57, 1712. doi: 10.1002/anie.201712019
48	Wang X. ; Li Y. ; Knecht T. ; Daniliuc C. G. ; Houk K. N. ; Glorius F. Angew. Chem. Int. Edit. 2018, 57, 5520. doi: 10.1002/anie.201800803
49	Zhou Z. ; Bian M. ; Zhao L. ; Gao H. ; Huang J. ; Liu X. ; Yu X. ; Li X. ; Yi W. Org. Lett. 2018, 20, 3892. doi: 10.1021/acs.orglett.8b01477
50	Liu G. ; Shen Y. ; Zhou Z. ; Lu X. Angew. Chem. Int. Edit. 2013, 52, 6033. doi: 10.1002/anie.201300881
51	Zhou Z. ; Liu G. ; Shen Y. ; Lu X. Org. Chem. Front. 2014, 1, 1161. doi: 10.1039/C4QO00196F
52	Chen Y. ; Wang D. ; Duan P. ; Ben R. ; Dai L. ; Shao X. ; Hong M. ; Zhao J. ; Huang Y. Nat. Commun. 2014, 5, 4610. doi: 10.1038/ncomms5610
53	Zhou Z. ; Liu G. ; Chen Y. ; Lu X. Org. Lett. 2015, 17, 5874. doi: 10.1021/acs.orglett.5b03060
54	Zhou J. ; Shi J. ; Qi Z. ; Li X. ; Xu H. E. ; Yi W. ACS Catal. 2015, 5, 6999. doi: 10.1021/acscatal.5b01571
55	Xie Y. Chem. Commun. 2016, 52, 12372. doi: 10.1039/c6cc05769a
56	Wang H. ; Wang B. ; Li B. J. Org. Chem. 2017, 82, 9560. doi: 10.1021/acs.joc.7b01566
57	Hu S. ; Lu L. ; Zhu T. ; Wu Q. ; Chen Y. ; Li J. J. ; Zhao J. Org. Biomol. Chem. 2017, 16, 43. doi: 10.1039/C7OB02438J
58	Li Y. ; Shi D. ; Tang Y. ; He X. ; Xu S. J. Org. Chem. 2018, 83, 9464. doi: 10.1021/acs.joc.8b01166
59	Chen W. ; Liu F.-X. ; Gong W. ; Zhou Z. ; Gao H. ; Shi J. ; Wu B. ; Yi W. Adv. Synth. Catal. 2018, 360, 2470. doi: 10.1002/adsc.201800322
60	Zhou W. ; Mei Y. L. ; Li B. ; Guan Z. Y. ; Deng Q. H. Org. Lett. 2018, 20, 5808. doi: 10.1021/acs.orglett.8b02504
61	Yi W. ; Chen W. ; Liu F.-X. ; Zhong Y. ; Wu D. ; Zhou Z. ; Gao H. ACS Catal. 2018, 9508. doi: 10.1021/acscatal.8b02402
62	Pan J. L. ; Xie P. ; Chen C. ; Hao Y. ; Liu C. ; Bai H. Y. ; Ding J. ; Wang L. R. ; Xia Y. ; Zhang S. Y. Org. Lett. 2018, 20, 7131. doi: 10.1021/acs.orglett.8b03082
63	Li M. ; Wang J. H. ; Li W. ; Wen L. R. Org. Lett. 2018, 20, 7694. doi: 10.1021/acs.orglett.8b03427
64	Hu F. ; Xia Y. ; Ye F. ; Liu Z. ; Ma C. ; Zhang Y. ; Wang J. Angew. Chem. Int. Edit. 2014, 53, 1364. doi: 10.1002/anie.201309650
65	Zhou J. ; Shi J. ; Liu X. ; Jia J. ; Song H. ; Xu H. E. ; Yi W. Chem. Commun. 2015, 51, 5868. doi: 10.1039/C5CC00354G
66	Hu Z. ; Liu G. Adv. Synth. Catal. 2017, 359, 1643. doi: 10.1002/adsc.201601296
67	Zhang Y. ; He Y. ; Li L. ; Ji M. ; Li X. Z. ; Zhu G. J. Org. Chem. 2018, 83, 2898. doi: 10.1021/acs.joc.8b00108
68	Wu Y. ; Chen Z. ; Yang Y. ; Zhu W. ; Zhou B. J. Am. Chem. Soc. 2018, 140, 42. doi: 10.1021/jacs.7b10349
69	Duan P. ; Yang Y. ; Ben R. ; Yan Y. ; Dai L. ; Hong M. ; Wu Y.-D. ; Wang D. ; Zhang X. ; Zhao J. Chem. Sci. 2014, 5, 1574. doi: 10.1039/C3SC53228C
70	Li B. ; Lan J. ; Wu D. ; You J. Angew. Chem. Int. Edit. 2015, 54, 1400. doi: 10.1002/anie.201507272
71	Li B. ; Tang G. ; Zhou L. ; Wu D. ; Lan J. ; Zhou L. ; Lu Z. ; You J. Adv. Funct. Mater. 2017, 27, 1605245. doi: 10.1002/adfm.201605245
72	Li B. ; Zhou L. ; Cheng H. ; Huang Q. ; Lan J. ; Zhou L. ; You J. Chem. Sci. 2018, 9, 1213. doi: 10.1039/c7sc04464j
73	Wu Q. ; Chen Y. ; Yan D. ; Zhang M. ; Lu Y. ; Sun W. Y. ; Zhao J. Chem. Sci. 2017, 8, 169. doi: 10.1039/C6SC03169B
74	Xiong F. ; Lu L. ; Sun T. Y. ; Wu Q. ; Yan D. ; Chen Y. ; Zhang X. ; Wei W. ; Lu Y. ; Sun W. Y. ; Li J. J. ; Zhao J. Nat. Commun. 2017, 8, 15912. doi: 10.1038/ncomms15912
75	Wang X. ; Gensch T. ; Lerchen A. ; Daniliuc C. G. ; Glorius F. J. Am. Chem. Soc. 2017, 139, 6506. doi: 10.1021/jacs.7b02725
76	Wu Q. ; Yan D. ; Chen Y. ; Wang T. ; Xiong F. ; Wei W. ; Lu Y. ; Sun W. Y. ; Li J. J. ; Zhao J. Nat. Commun. 2017, 8, 14227. doi: 10.1038/ncomms14227
77	Yan D. ; Wang G. ; Xiong F. ; Sun W. Y. ; Shi Z. ; Lu Y. ; Li S. ; Zhao J. Nat. Commun. 2018, 9, 4293. doi: 10.1038/s41467-018-06763-4

[1]	Zhen WANG,En LI,Zhiqi HE,Jiean CHEN,Yong HUANG. Dehydrogenative Annulation of γ, δ-Unsaturated Amides and Alkynes via Double C―H Activation [J]. Acta Physico-Chimica Sinica, 2019, 35(9): 906-912.
[2]	Mengdi ZHAO,Wenjun LU. Alkanes Functionalization via C―H Activation [J]. Acta Physico-Chimica Sinica, 2019, 35(9): 977-988.
[3]	Yuanyuan HU,Congyang WANG. Bimetallic C―H Activation in Homogeneous Catalysis [J]. Acta Physico-Chimica Sinica, 2019, 35(9): 913-922.
[4]	Dong CHEN,Xinyang YUE,Xunlu LI,Xiaojing WU,Yongning ZHOU. Research Progress of Cathode Materials for Lithium-Selenium Batteries [J]. Acta Phys. -Chim. Sin., 2019, 35(7): 667-683.
[5]	Lulu LI,Lu YAO,Li DUAN. Application of Lithium-Selenium Batteries Using Covalent Organic Framework Composite Cathodes [J]. Acta Phys. -Chim. Sin., 2019, 35(7): 734-739.
[6]	Wen LUO,Lei HUANG,Dou-Dou GUAN,Ru-Han HE,Feng LI,Li-Qiang MAI. A Selenium Disulfide-Impregnated Hollow Carbon Sphere Composite as a Cathode Material for Lithium-Ion Batteries [J]. Acta Phys. -Chim. Sin., 2016, 32(8): 1999-2006.
[7]	Zhi-Jian. LIAO,Zhen-Li. QIN,Si-Nan. DU,Si-Yu. LI,Guan-Hou. CHEN,Fang. ZUO,Jian-Bin. LUO. Orientational Transitions of Liquid Crystal Driven by Hydrogen-Bond Interaction at the Liquid Crystal-Aqueous Interface [J]. Acta Phys. -Chim. Sin., 2015, 31(9): 1733-1740.
[8]	ZHOU Dan-Hong, LI Miao-Miao, CUI Li-Li. Photophysical Properties and Photoinduced Electron Transfer Mechanism in a Near-IR Fluorescent Probe for Monitoring Peroxynitrite [J]. Acta Phys. -Chim. Sin., 2013, 29(07): 1453-1460.
[9]	ZHOU Liang-Chun, MENG Xiang-Guang, LI Jian-Mei, HU Wei, LIU Bo, DU Juan. Kinetics and Thermodynamics of Adsorption of Chlorophenols onto β-Cyclodextrin Modified Chitosan [J]. Acta Phys. -Chim. Sin., 2012, 28(07): 1615-1622.
[10]	RAO Gui-Shi, CHENG Mei-Qin, ZHONG Yan, DENG Xiao-Cong, YI Fei, CHEN Zhi-Ren, ZHONG Qi-Ling, FAN Feng-Ru, REN Bin, TIAN Zhong-Qun. Preparation of High Catalytic Platinum Hollow Nanospheres and Their Electrocatalytic Performance for Methanol Oxidation [J]. Acta Phys. -Chim. Sin., 2011, 27(10): 2373-2378.
[11]	GUO Zhi-Jun, CHEN Zong-Yuan, WU Wang-Suo, LIU Chun-Li, CHEN Tao, TIAN Wen-Yu, LI Chun. Adsorption of Se(IV) onto Beishan Granite [J]. Acta Phys. -Chim. Sin., 2011, 27(09): 2222-2226.
[12]	LIAO Cheng, HAN Jun-Feng, JIANG Tao, XIE Hua-Mu, JIAO Fei, ZHAO Kui. Effect of Se Vapor Concentration on CIGS Film Preparation [J]. Acta Phys. -Chim. Sin., 2011, 27(02): 432-436.
[13]	SUN Qian, WANG Jin-Ting, ZHANG Li-Min, YANG Mao-Ping. Photoinduced Electron and Hydrogen Transfer Reactions of Thioxanthone with Amines, Phenols and Alcohols [J]. Acta Phys. -Chim. Sin., 2010, 26(09): 2481-2488.
[14]	Huang Jian-Gou;Xu Man-Cai;Li Hai-Tao;Shi Zuo-Qing;He Bing-Lin. Adsorption Thermodynamics of Macroporous Cross-linked Poly (N-methyl-N-p- vinylbenzylacetamine) Resin for Phenols from Non-aqueous System [J]. Acta Phys. -Chim. Sin., 2003, 19(03): 208-211.
[15]	Li Xi, Liu Yi, Wu Jun, Zhao Ru-Ming, Qu Song-Sheng. Microcalorimetric Study of the Action of Selenium-containing Complexes on Growth Metabolism of Escherichia coli [J]. Acta Phys. -Chim. Sin., 2000, 16(06): 568-572.

Research Advances in C―H Bond Activation of Multitasking N-Phenoxyamides

RichHTML

PDF

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 38

References 77

Related Articles 15

Metrics

Recommended 0