Silver-Promoted Regioselective Oxidative Decarboxylative C–H Alkylation of Phenanthridines with Carboxylic Acids

Tianyin Huang; Yang Yu; Hui Wang; Yifan Lin; Yurui Ma; Haoyu Wang; Chang-Hua Ding; Junjie Xiao; Bin Xu

doi:10.1055/s-0039-1690220

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(02): 239-245
DOI: 10.1055/s-0039-1690220

paper

Silver-Promoted Regioselective Oxidative Decarboxylative C–H Alkylation of Phenanthridines with Carboxylic Acids

Tianyin Huang

^aDepartment of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China eMail: dingchanghua@shu.edu.cn eMail: junjiexiao@live.cn eMail: xubin@shu.edu.cn

,

Yang Yu

^aDepartment of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China eMail: dingchanghua@shu.edu.cn eMail: junjiexiao@live.cn eMail: xubin@shu.edu.cn

,

Hui Wang

^aDepartment of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China eMail: dingchanghua@shu.edu.cn eMail: junjiexiao@live.cn eMail: xubin@shu.edu.cn

,

Yifan Lin

^aDepartment of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China eMail: dingchanghua@shu.edu.cn eMail: junjiexiao@live.cn eMail: xubin@shu.edu.cn

,

Yurui Ma

^aDepartment of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China eMail: dingchanghua@shu.edu.cn eMail: junjiexiao@live.cn eMail: xubin@shu.edu.cn

,

Haoyu Wang

^aDepartment of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China eMail: dingchanghua@shu.edu.cn eMail: junjiexiao@live.cn eMail: xubin@shu.edu.cn

,

Chang-Hua Ding ∗

^aDepartment of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China eMail: dingchanghua@shu.edu.cn eMail: junjiexiao@live.cn eMail: xubin@shu.edu.cn

,

Junjie Xiao∗

^aDepartment of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China eMail: dingchanghua@shu.edu.cn eMail: junjiexiao@live.cn eMail: xubin@shu.edu.cn

,

Bin Xu∗

^aDepartment of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China eMail: dingchanghua@shu.edu.cn eMail: junjiexiao@live.cn eMail: xubin@shu.edu.cn

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

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Abstract

Alle Artikel dieser Rubrik

^§ These authors contributed equally to this manuscript

Abstract

A novel oxidative decarboxylative C–H alkylation of phenanthridines with carboxylic acids was developed for the efficient synthesis of multi-substituted phenanthridine derivatives. The given method features easy availability of starting materials, high regioselectivity, and mild conditions. Furthermore, a one-pot synthesis of multi-substituted phenanthridine derivatives was realized by the reaction of biphenyl isocyanides and carboxylic acid.

Key words

phenanthridine - decarboxylation - silver acetate - C–H alkylation - potassium persulfate - late-stage modification

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Referenzen

References

1a Krane BD, Fagbule MO, Shamma M. J. Nat. Prod. 1984; 47: 1
1b Ishikawa T. Med. Res. Rev. 2001; 21: 61
1c Lewis WG, Green LG, Grynszpan F, Radić Z, Carlier PR, Taylor P, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 1053
1d Dvořák Z, Kubán V, Klejdus B, Vičar J, Ulrichová J, Hlaváč J, Šimánek V. Heterocycles 2006; 68: 2403
1e Slaninová I, Pěnčíková K, Urbanová J, Slanina J, Táborská E. Phytochem. Rev. 2014; 13: 51
1f Wang X, Tanaka M, Krstin S, Peixoto H, Wink M. Molecules 2016; 21: 906
1g Galadari S, Rahman A, Pallichankandy S, Thayyullathil F. Phytomedicine 2017; 34: 143

2a Lynch MA, Duval O, Sukhanova A, Devy J, MacKay SP, Waigh RD, Nabiev I. Bioorg. Med. Chem. Lett. 2001; 11: 2643
2b Abdel-Halim OB, Morikawa T, Ando S, Matsuda H, Yoshikawa M. J. Nat. Prod. 2004; 67: 1119
2c Bernardo PH, Wan K.-F, Sivaraman T, Xu J, Moore FK, Hung AW, Mok HY. K, Yu VC, Chai CL. L. J. Med. Chem. 2008; 51: 6699

For selected examples see:

3a Kessar SV, Gupta YP, Balakrishnan P, Sawal KK, Mohammad T, Dutt M. J. Org. Chem. 1988; 53: 1708
3b Lysén M, Kristensen JL, Vedsø P, Begtrup M. Org. Lett. 2002; 4: 257
3c Pawlas J, Begtrup M. Org. Lett. 2002; 4: 2687
3d Gerfaud T, Neuville L, Zhu JP. Angew. Chem. Int. Ed. 2009; 48: 572
3e Zhang L, Ang GY, Chiba S. Org. Lett. 2010; 12: 3682
3f Linsenmeier AM, Williams CM, Bräse S. J. Org. Chem. 2011; 76: 9127
3g Deb I, Yoshikai N. Org. Lett. 2013; 15: 4254
3h Read ML, Gundersen LL. J. Org. Chem. 2013; 78: 1311
3i Wang WY, Feng X, Hu BL, Deng CL, Zhang XG. J. Org. Chem. 2013; 78: 6025
3j Chen Y.-F, Hsieh J.-C. Org. Lett. 2014; 16: 4642
3k Han W, Zhou X, Yang S, Xiang G, Cui B, Chen Y. J. Org. Chem. 2015; 80: 11580
3l Tang CH, Yuan YZ, Jiao N. Org. Lett. 2015; 17: 2206
3m Zhang C, Li T, Wang L, Rao Y. Org. Chem. Front. 2017; 4: 386
3n Xi J, Dong Q.-L, Liu G.-S, Wang S, Chen L, Yao Z.-J. Synlett 2010; 1674

For selected reviews, see:

4a Qiu G, Ding Q, Wu J. Chem. Soc. Rev. 2013; 42: 5257
4b Zhang B, Studer A. Chem. Soc. Rev. 2015; 44: 3505
4c Wang H, Xu B. Chin. J. Org. Chem. 2015; 35: 588
4d Song B, Xu B. Chem. Soc. Rev. 2017; 46: 1103

For selected examples, see:

4e Nanni D, Pareschi P, Rizzoli C, Sgarabotto P, Tundo A. Tetrahedron 1995; 51: 9045
4f Tobisu M, Koh K, Furukawa T, Chatani N. Angew. Chem. Int. Ed. 2012; 51: 11363
4g Zhang B, Mück-Lichtenfeld C, Daniliuc CG, Studer A. Angew. Chem. Int. Ed. 2013; 52: 10792
4h Cheng Y, Jiang H, Zhang Y, Yu S. Org. Lett. 2013; 15: 5520
4i Liu J, Fan C, Yin H, Qin C, Zhang G, Zhang X, Yi H, Lei A. Chem. Commun. 2014; 50: 2145
4j Sha W, Yu J.-T, Jiang Y, Yang H, Cheng J. Chem. Commun. 2014; 50: 9179
4k Xia Z, Huang J, He Y, Zhao J, Lei J, Zhu Q. Org. Lett. 2014; 16: 2546
4l Gu J.-W, Zhang X. Org. Lett. 2015; 17: 5384
4m Rong J, Deng L, Tan P, Ni C, Gu Y, Hu J. Angew. Chem. Int. Ed. 2016; 55: 2743
4n Guo A, Han J.-B, Tang X.-Y. Org. Lett. 2018; 20: 2351
4o Rohe S, McCallum T, Morris AO, Barriault L. J. Org. Chem. 2018; 83: 10015

For selected reviews, see:

5a Minisci F. Synthesis 1973; 1
5b Rodríguez N, Goossen LJ. Chem. Soc. Rev. 2011; 40: 5030
5c Duncton MA. J. Med. Chem. Commun. 2011; 2: 1135

For selected examples, see:

6a Bi H.-P, Zhao L, Liang Y.-M, Li C.-J. Angew. Chem. Int. Ed. 2009; 48: 792
6b Jia W, Jiao N. Org. Lett. 2010; 12: 2000
6c Luo Y, Wu J. Chem. Commun. 2010; 46: 3785
6d Zhang Y, Patel S, Mainolfi N. Chem. Sci. 2012; 3: 3196
6e Bhadra S, Dzik WI, Goossen LJ. J. Am. Chem. Soc. 2012; 134: 9938
6f Yin F, Wang Z, Li Z, Li C. J. Am. Chem. Soc. 2012; 134: 10401
6g Wang H, Guo L.-N, Duan X.-H. Adv. Synth. Catal. 2013; 355: 2222
6h Mai W.-P, Wang J.-T, Yang L.-R, Yuan J.-W, Xiao Y.-M, Mao P, Qu L.-B. Org. Lett. 2014; 16: 204
6i Zhao W.-M, Chen X.-L, Yuan J.-W, Qu L.-B, Duan L.-K, Zhao Y.-F. Chem. Commun. 2014; 50: 2018
6j Shi G, Shao C, Pan S, Yu J, Zhang Y. Org. Lett. 2015; 17: 38
6k Zhu Y, Li X, Wang X, Huang X, Shen T, Zhang Y, Sun X, Zou M, Song S, Jiao N. Org. Lett. 2015; 17: 4702
6l Liu C, Wang X, Li Z, Cui L, Li C. J. Am. Chem. Soc. 2015; 137: 9820
6m Li M, Hoover JM. Chem. Commun. 2016; 52: 8733

7 Minisci F, Bernardi R, Bertini F, Galli R, Perchinummo M. Tetrahedron 1971; 27: 3575

8a Xu S, Huang X, Hong X, Xu B. Org. Lett. 2012; 14: 4614
8b Fang T, Tan Q, Ding Z, Liu B, Xu B. Org. Lett. 2014; 16: 2342
8c Qian G, Hong X, Liu B, Mao H, Xu B. Org. Lett. 2014; 16: 5294
8d Huang X, Xu S, Tan Q, Gao M, Li M, Xu B. Chem. Commun. 2014; 50: 1465
8e Hong X, Wang H, Qian G, Tan Q, Xu B. J. Org. Chem. 2014; 79: 3228
8f Gao M, Li Y, Gan Y, Xu B. Angew. Chem. Int. Ed. 2015; 54: 8795
8g Mao H, Gao M, Liu B, Xu B. Org. Chem. Front. 2016; 3: 516
8h Hong X, Tan Q, Liu B, Xu B. Angew. Chem. Int. Ed. 2017; 56: 3961
8i Tian Z, Xu J, Liu B, Tan Q, Xu B. Org. Lett. 2018; 20: 2603

9 CCDC 1921522 (3k) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

10a Anderson JM, Kochi JK. J. Am. Chem. Soc. 1970; 92: 1651
10b Anderson JM, Kochi JK. J. Org. Chem. 1970; 35: 986
10c Liu X, Wang Z, Cheng X, Li C. J. Am. Chem. Soc. 2012; 134: 14330
10d Fang G, Cong X, Zanoni G, Liu Q, Bi X. Adv. Synth. Catal. 2017; 359: 1422
10e Mandal S, Bera T, Dubey G, Saha J, Laha JK. ACS Catal. 2018; 8: 5085

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