Synthesis of Dibenzo[f,h]quinolines by Stepwise C–H Arylation of 2-Phenylpyridine and Reductive Cyclodehydrogenation

Yan-Qin He; Zhong-Qiu Li; Yu-Wu Zhong

doi:10.1055/a-2069-4269

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(17): 2779-2785
DOI: 10.1055/a-2069-4269

paper

Special Issue Honoring Prof. Guoqiang Lin's Contributions to Organic Chemistry

Synthesis of Dibenzo[f,h]quinolines by Stepwise C–H Arylation of 2-Phenylpyridine and Reductive Cyclodehydrogenation

Yan-Qin He

^aBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, 2 Bei Yi Jie, Zhong Guan Cun, Haidian District, Beijing 100190, P. R. of China

^bInstitute of BioPharmaceutical Research, Liaocheng University, Liaocheng, Shandong 252059, P. R. of China

,

Zhong-Qiu Li

^aBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, 2 Bei Yi Jie, Zhong Guan Cun, Haidian District, Beijing 100190, P. R. of China

,

Yu-Wu Zhong ∗

^aBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, 2 Bei Yi Jie, Zhong Guan Cun, Haidian District, Beijing 100190, P. R. of China

^cSchool of Chemical Sciences, University of Chinese Academy of Sciences, No.19(A) Yuquan Road, Shijingshan District, Beijing 100049, P. R. of China

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Abstract

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Dedicated to Prof. Guo-Qiang Lin on the occasion of his 80^th birthday.

Abstract

A synthetic approach to dibenzo[f,h]quinolines and their derivatives via stepwise ruthenium-catalyzed C–H arylation and potassium-mediated reductive cyclodehydrogenation from 2-phenylpyridine and aryl bromides, is presented. One dibenzo[f,h]quinoline derivative is used as a bidentate ligand to prepare a cyclometalated ruthenium complex. Two dibenzo[f,h]quinoline compounds and the ruthenium complex were characterized by single-crystal X-ray structural analysis.

Key words

dibenzo[f,h]quinolones - polycyclic aromatic hydrocarbons - C–H arylation - reductive cyclodehydrogenation - ruthenium

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Referenzen

References

1a Watson MD, Fechtenkotter A, Mullen K. Chem. Rev. 2001; 101: 1267
1b Ito H, Ozaki K, Itami K. Angew. Chem. Int. Ed. 2017; 56: 11144

2a Li C, Liu MY, Pschirer NG, Baumgarten M, Mullen K. Chem. Rev. 2010; 110: 6817
2b Zhu Q, Kan C, Cao Y, Tang Z, Ku K, Hang P, Li B, Yao Y, Lei M, Yu X. Org. Lett. 2022; 24: 7053

3 Gunes S, Neugebauer H, Sariciftci NS. Chem. Rev. 2007; 107: 1324
4 Allard S, Forster M, Souharce B, Thiem H, Scherf U. Angew. Chem. Int. Ed. 2008; 47: 4070
5 Wei J, Han B, Guo Q, Shi X, Wang W, Wei N. Angew. Chem. Int. Ed. 2010; 49: 8209

6a Anthony JE. Chem. Rev. 2006; 106: 5028
6b Li J, Zhang Q. ACS Appl. Mater. Interfaces 2015; 7: 28049
6c Bunz UH. F, Freudenberg J. Acc. Chem. Res. 2019; 52: 1575

7a Jafari F, Baghayi H, Lavaee P, Hadizadeh F, Soltani F, Moallemzadeh H, Mirzaei S, Aboutorabzadeh SM, Ghodsi R. Eur. J. Med. Chem. 2019; 164: 292
7b Yang CW, Lee YZ, Kang IJ, Barnard DL, Jan JT, Lin D, Huang CW, Yeh TK, Chao YS, Lee SJ. Antiviral Res. 2010; 88: 160

8 Lee YZ, Yang CW, Hsu HY, Qiu YQ, Yeh TK, Chang HY, Chao YS, Lee SJ. J. Med. Chem. 2012; 55: 10363

9a Elferink VH. M, Bos HJ. T. J. Chem. Soc., Chem. Commun. 1985; 882
9b Gerosa GG, Schwengers SA, Maji R, De CK, List B. Angew. Chem. Int. Ed. 2020; 59: 20485
9c Krueger J, Mosettig E. J. Org. Chem. 1940; 5: 313
9d Nicolaides DN, Awad RW, Papageorgiou GK, Stephanidoustephanatou J. J. Org. Chem. 1994; 59: 1083
9e Nicolaides DN, BezergiannidouBalouctsi C, Awad RW, Litinas KE, MalamidouXenikaki E, Terzis A, Raptopoulou CP. J. Org. Chem. 1997; 62: 499

10 Hewlins M, Salter R. Synthesis 2007; 2157

11a Bilgic O, Young DW. J. Chem. Soc., Perkin Trans. 1 1980; 1233
11b Campos PJ, Anon E, Malo MC, Rodriguez MA. Tetrahedron 1998; 54: 14113

12 Nagao I, Shimizu M, Hiyama T. Angew. Chem. Int. Ed. 2009; 48: 7573
13 McIver A, Young DD, Deiters A. Chem. Commun. 2008; 44: 4750

14a Yang S, Hua WK, Wu YQ, Hu T, Wang F, Zhang XX, Zhang FZ. Chem. Commun. 2018; 54: 3239
14b Cheng SL, Fan XY, Zhu JF, Wang BQ, Shi Y, Feng C, Xiang SK. Org. Biomol. Chem. 2022; 20: 8657

15 Zeng Z, Jin H, Sekine K, Rudolph M, Rominger F, Hashmi AS. K. Angew. Chem. Int. Ed. 2018; 57: 6935
16 Chakraborty B, Kar A, Chanda R, Jana U. J. Org. Chem. 2020; 85: 9281
17 Lee JB, Kim GH, Jeon JH, Jeong SY, Lee S, Park J, Lee D, Kwon Y, Seo JK, Chun JH, Kang SJ, Choe W, Rohde JU, Hong SY. Nat. Commun. 2022; 13: 2421

18a Badger GM, Sasse WH. Adv. Heterocycl. Chem. 1963; 18: 179
18b Nareddy P, Jordan F, Szostak M. ACS Catal. 2017; 7: 5721

19 Schlichting P, Rohr U, Mullen K. J. Mater. Chem. 1998; 8: 2651
20 Wang CS, Sun Q, Garcia F, Wang C, Yoshikai N. Angew. Chem. Int. Ed. 2021; 60: 9627
21 Kawahara KP, Matsuoka W, Ito H, Itami K. Angew. Chem. Int. Ed. 2020; 59: 6383

22a Ackermann L, Vicente R, Althammer A. Org. Lett. 2008; 10: 2299
22b Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
22c He Y.-Q, Zhong Y.-W. Chem. Commun. 2015; 51: 3411

23 Grzybowski M, Skonieczny K, Butenschon H, Gryko DT. Angew. Chem. Int. Ed. 2013; 52: 9900

24a Rickhaus M, Belanger AP, Wegner HA, Scott LT. J. Org. Chem. 2010; 75: 7358
24b Gryko DT, Piechowska J, Galezowski M. J. Org. Chem. 2010; 75: 1297
24c Firmansyah D, Banasiewicz M, Deperasinska I, Makarewicz A, Kozankiewicz B, Gryko DT. Chem. Asian J. 2014; 9: 2483

25a Bossi A, Rausch AF, Leitl MJ, Czerwieniec R, Whited MT, Djurovich PI, Yersin H, Thompson ME. Inorg. Chem. 2013; 52: 12403
25b Zhong Y.-W. Chin. J. Chem. 2021; 39: 543
25c Shao J.-Y, Gong Z.-L, Zhong Y.-W. Dalton Trans. 2018; 23
25d Yang W.-W, Zhong Y.-W, Yoshikawa S, Shao J.-Y, Masaoka S, Sakai K, Yao J, Haga M.-A. Inorg. Chem. 2012; 51: 890

26a Binnani C, Mandal SC, Pathak B, Singh SK. Eur. J. Inorg. Chem. 2019; 2844
26b Jagtap RA, Soni V, Punji B. ChemSusChem 2017; 10: 2242
26c Binnani C, Tyagi D, Rai RK, Mobin SM, Singh SK. Chem. Asian J. 2016; 11: 3022

27a Ackermann L, Vicente R, Potukuchi HK, Pirovano V. Org. Lett. 2010; 12: 5032
27b Punji B, Song W, Shevchenko GA, Ackermann L. Chem. Eur. J. 2013; 19: 10605

28 Kaloğlu N, Özdemir İ, Gürbüz N, Arslan H, Dixneuf PH. Molecules 2018; 23: 647

29a Yu W.-Y, Sit WN, Zhou Z, Chan AS. C. Org. Lett. 2009; 11: 3174
29b Chu J.-H, Tsai S.-L, Wu M.-J. Synthesis 2009; 3757

30a Yu T.-Y, Xu W.-H, Lu H, Wei H. Chem. Sci. 2020; 11: 12336
30b Qi Z, Li X. Angew. Chem. Int. Ed. 2013; 52: 8995

31a Wagner CJ, Salisbury EA, Schoonover EJ, VanderRoest JP, Johnson JB. Tetrahedron Lett. 2021; 73: 153132
31b Jagtap RA, Soni V, Punji B. ChemSusChem 2017; 10: 2242

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