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

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

Publication History

Received: 26 February 2023

Accepted after revision: 05 April 2023

Accepted Manuscript online:
05 April 2023

Article published online:
08 May 2023

• 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