Copper(II)-Mediated Cascade Oxidative C–C Coupling and Aromatization: Synthesis of 3-Hydroxyphenanthridinone Derivatives

Qingzhen Yu; Nan Zhang; Yang Tang; Hang Lu; Jianhui Huang; Songqing Wang; Yunfei Du; Kang Zhao

doi:10.1055/s-0032-1316542

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(15): 2374-2384
DOI: 10.1055/s-0032-1316542

paper

Copper(II)-Mediated Cascade Oxidative C–C Coupling and Aromatization: Synthesis of 3-Hydroxyphenanthridinone Derivatives

Qingzhen Yu

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

,

Nan Zhang

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

,

Yang Tang

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

,

Hang Lu

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

,

Jianhui Huang

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

,

Songqing Wang

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

,

Yunfei Du*

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

,

Kang Zhao*

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A novel copper(II) acetate mediated synthesis of 3-hydroxyphenanthridin-6(5H)-ones from N-(3-oxocyclohex-1-enyl)benzamides was developed. The process is postulated to involve an intramolecular oxidative C(sp²)–C(sp³) bond formation followed by dehydrogenative aromatization.

Key words

copper(II) acetate - phenanthridinone - C–H functionalization - C–C oxidative coupling - dehydrogenative aromatization

Volltext

Referenzen

References

For recent reviews on C–C bond formation, see:

1a Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
1b Liu C, Zhang H, Shi W, Lei A.-W. Chem. Rev. 2011; 111: 1780
1c Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
1d Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
1e Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
1f Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
1g Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792

For selected examples on C–C cross-coupling, see:

2a Stuart DR, Fagnou K. Science 2007; 316: 1172
2b Li B.-J, Tian S.-L, Fang Z, Shi Z.-J. Angew. Chem. Int. Ed. 2008; 47: 1115
2c Yeung CS, Zhao X.-D, Nadine B, Dong VM. Chem. Sci. 2010; 1: 331
2d Zhao X.-D, Yeung CS, Dong VM. J. Am. Chem. Soc. 2010; 132: 5837
2e Stuart DR, Villemure E, Fagnou K. J. Am. Chem. Soc. 2007; 129: 12072
2f Cho SH, Hwang SJ, Chang S. J. Am. Chem. Soc. 2008; 130: 9254
2g Hull KL, Sanford MS. J. Am. Chem. Soc. 2009; 131: 9651
2h Hull KL, Sanford MS. J. Am. Chem. Soc. 2007; 129: 11904
2i Dwight TA, Rue NR, Charyk D, Josselyn R, DeBoef B. Org. Lett. 2007; 9: 3137
2j Brasche G, Fortanet JG, Buchwald SL. Org. Lett. 2008; 10: 2207
2k Li R, Jiang L, Lu W.-J. Organometallics 2006; 25: 5973
2l Shi Z.-Z, Zhang C, Li S, Pan D.-L, Ding S.-T, Cui Y.-X, Jiao N. Angew. Chem. Int. Ed. 2009; 48: 4572
2m Stuart DR, Alsabeh P, Kuhn M, Fagnou K. J. Am. Chem. Soc. 2010; 132: 18326
2n Martinez R, Simon M.-O, Chevalier R, Pautigny C, Genet J.-P, Darses S. J. Am. Chem. Soc. 2009; 131: 7887
2o Inoue S, Shiota H, Fukumoto Y, Chatani N. J. Am. Chem. Soc. 2009; 131: 6898

For selected examples, see:

3a Evano G, Blanchard N, Toumi M. Chem. Rev. 2008; 108: 3054
3b He C, Guo S, Huang L, Lei A.-W. J. Am. Chem. Soc. 2010; 132: 8273
3c Do H.-Q, Daugulis O. J. Am. Chem. Soc. 2008; 130: 1128
3d Li Z.-P, Li C.-J. J. Am. Chem. Soc. 2004; 126: 11810
3e Li Z.-P, Li C.-J. J. Am. Chem. Soc. 2005; 127: 6968
3f Li Z.-P, Li C.-J. J. Am. Chem. Soc. 2005; 127: 3672
3g Li Z.-P, Li C.-J. Org. Lett. 2004; 6: 4997
3h Kawano T, Yoshizumi T, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 3072
3i Yang F.-Z, Xu Z.-Q, Wang Z, Yu Z.-K, Wang R. Chem.–Eur. J. 2011; 17: 6321
3j Wendlandt AE, Suess AM, Stahl SS. Angew. Chem. Int. Ed. 2011; 50: 11062
3k Zhang C, Xu Z.-J, Zhang L.-R, Jiao N. Angew. Chem. Int. Ed. 2011; 50: 11088
3l Bernini R, Fabrizi G, Sferrazza A, Cacchi S. Angew. Chem. Int. Ed. 2009; 48: 8078

For selected examples, see:

4a Shibasaki M, Kanai M. Chem. Rev. 2008; 108: 2853
4b Zhang Y.-H, Li C.-J. Angew. Chem. Int. Ed. 2006; 45: 1949
4c Jia Y.-X, Kündig EP. Angew. Chem. Int. Ed. 2009; 48: 1636
4d Tang B.-X, Song R.-J, Wu C.-Y, Liu Y, Zhou M.-B, Wei W.-T, Deng G.-B, Yin D.-L, Li J.-H. J. Am. Chem. Soc. 2010; 132: 8900
4e Perry A, Taylor RJ. K. Chem. Commun. 2009; 3249
4f Klein JE. M. N, Perry A, Pugh DS, Taylor RJ. K. Org. Lett. 2010; 12: 3446
4g Guru MM, Ali MA, Punniyamurthy T. Org. Lett. 2011; 13: 1194
4h Zhang C, Jiao N. J. Am. Chem. Soc. 2010; 132: 28

5a Dow RL, Chou TT, Bechle BM, Goddard C, Larson ER. J. Med. Chem. 1994; 37: 2224
5b Kanojia RM, Ohemeng KA, Schwender CF, Barrett JF. Tetrahedron Lett. 1995; 36: 8553

For selected examples on the synthesis of phenanthridinones by Pd(OAc)₂, see:

6a Karthikeyan J, Cheng C.-H. Angew. Chem. Int. Ed. 2011; 50: 9880
6b Wang G.-W, Yuan T.-T, Li D.-D. Angew. Chem. Int. Ed. 2011; 50: 1380
6c Donati L, Michel S, Tillequin F, Porée F.-H. Org. Lett. 2010; 12: 156
6d Furuta T, Kitamura Y, Hashimoto A, Fujii S, Tanaka K, Kan T. Org. Lett. 2007; 9: 183
6e Harayama T, Asai M, Miyagoe T, Abe H, Takeuchi Y, Yamaguchi A, Fujii S. Heterocycles 2010; 81: 1881
6f Majumdar KC, Chattopadhyay B, Nath S. Tetrahedron Lett. 2008; 49: 1609
6g Bernini R, Cacchi S, Fabrizi G, Sferrazza A. Synthesis 2008; 729
6h Black DS. C, Keller PA, Kumar N. Tetrahedron 1993; 49: 151
6i For an example on the synthesis of phenanthri-dinones by PIFA, see: Moreno I, Tellitu I, Etayo J, SanMartín R, Dimínguez E. Tetrahedron 2001; 57: 5403

7 Bi W.-Y, Yun X.-L, Fan Y.-F, Qi X.-X, Du Y.-F, Huang J.-H. Synlett 2010; 2899
8 Wang G.-W, Miao C.-B. Green Chem. 2006; 8: 1080

For the synthesis of substrate, see:

9a Montalbetti CA. G. N, Falque V. Tetrahedron 2005; 61: 10827
9b Anderson AJ, Nicholson JM, Bakare O, Butcher RJ, Wilson TL, Scott KR. Bioorg. Med. Chem. 2006; 14: 997
9c Zhang W, Pugh G. Tetrahedron 2003; 59: 3009

For some examples on the use of Cu(OAc)₂, see:

10a Würtz S, Rakshit S, Neumann JJ, Dröge T, Glorius F. Angew. Chem. Int. Ed. 2008; 47: 7230
10b Neumann JJ, Rakshit S, Dröge T, Würtz S, Glorius F. Chem.–Eur. J. 2011; 17: 7298

11 We thank one reviewer for suggesting such non-metallic hypervalent iodine oxidants for this cross-coupling and dehydrogenative reaction.
12 In order to further study the substrate scope, we also managed to prepare the substrates containing the bulky isopropyl and tert-butyl groups. However, attempts to prepare such compounds under various condensation conditions were not successful
13 For the previous examples describing such C(sp²)–C(sp²) bond coupling mediated by Pd, see refs. 2c, 6a, and 6h
14 For a previous example involving the Cu(II)-mediated SET process, see ref. 4c
15 Ninomiya BI, Naito T, Kiguchi T. J. Chem. Soc., Perkin Trans. 1 1973; 2257

16a Ueda S, Nagasawa H. J. Org. Chem. 2009; 74: 4272
16b Faler CA, Joullié MM. Tetrahedron Lett. 2006; 47: 7229

Zusatzmaterial

Supporting Information