CC BY ND NC 4.0 · SynOpen 2017; 01(01): 0129-0137
DOI: 10.1055/s-0036-1591503
paper
Copyright with the author

Pd/C-Catalyzed Intramolecular C–H Arylation for the Synthesis of Phenanthridinones and Dibenzo-α-pyrones

Lingyu Zhao*
,
Guodong Shen*
,
Tongxin Zhang
,
Zhen Wang
,
Yuhua Liang
This work was financially supported by the National Natural Science Foundation of China (No. 21402079) and the Research Fund for the Doctoral Program of Liaocheng University (No. 318051403 and 318051419).
Further Information

Publication History

Received: 06 September 2017

Accepted: 04 October 2017

Publication Date:
20 October 2017 (online)

Abstract

Pd/C was found to be an efficient and convenient metal catalyst for intramolecular C–H arylation reactions in the synthesis of phenanthridinones and dibenzo-α-pyrones. A variety of phenanthridinones and dibenzo-α-pyrones were synthesized under the highly active catalytic system of Pd/C-KOAc-DMA in moderate to excellent yields. The high catalytic activity, high recyclability, low costs, and ease of removal of Pd/C, combined with its commercial availability, render this protocol attractive for both synthetic and industrial applications.

 
  • References

    • 1a Nakamura M. Aoyama A. Salim MT. A. Okamoto M. Baba M. Miyachi H. Hashimoto Y. Aoyam H. Bioorg. Med. Chem. 2010; 18: 2402
    • 1b Ghosal S. Rao PH. Jaiswal DK. Kumar Y. Frahm AW. Phytochemistry 1981; 20: 2003
    • 1c Patil S. Kamath S. Sanchez T. Neamati N. Schinazi RF. Buolamwini JK. Bioorg. Med. Chem. 2007; 15: 1212
    • 1d Holl V. Coelho D. Weltin D. Hyun JW. Dufour P. Bischoff P. Anticancer Res. 2000; 20: 3233
    • 2a Aly AH. Edrada-Ebel R. Indriani ID. Wray V. Müller WE. G. Totzke F. Zirrgiebel U. Schächtele C. Kubbutat MH. G. Lin WH. Proksch P. Ebel R. J. Nat. Prod. 2008; 71: 972
    • 2b Mao Z. Sun W. Fu L. Luo H. Lai D. Zhou L. Molecules 2014; 19: 5088
    • 2c Bialonska D. Kasimsetty SG. Khan SI. Ferreira D. J. Agric. Food Chem. 2009; 57: 10181
    • 2d Griffin GF. Chu FS. Appl. Environ. Microbiol. 1983; 46: 1420
    • 2e Chu FS. J. Am. Oil Chem. Soc. 1981; 58: 1006
    • 2f Maeda N. Kokai Y. Ohtani S. Sahara H. Kuriyama I. Kamisuki S. Takahashi S. Sakaguchi K. Sugawara F. Yoshida H. Biochem. Biophys. Res. Commun. 2007; 352: 390
  • 3 Halim SA. Ibrahim MA. J. Mol. Struct. 2017; 1130: 543
  • 4 Qiang XX. Wu T. Fan JL. Wang JY. Song FL. Sun SG. Jiang JY. Peng XJ. J. Mater. Chem. 2012; 22: 16078
    • 5a Harayama T. Yasuda H. Heterocycles 1997; 46: 61
    • 5b Harayama T. Yasuda H. Akiyama T. Takeuchi Y. Abe H. Chem. Pharm. Bull. 2000; 48: 861
    • 5c Qabaja G. Jones GB. J. Org. Chem. 2000; 65: 7187
  • 6 Parisien M. Valette D. Fagnou K. J. Org. Chem. 2005; 70: 7578
  • 7 Yanagisawa S. Ueda K. Taniguchi T. Itami K. Org. Lett. 2008; 10: 4673
    • 8a Sun CL. Li H. Yu DG. Yu M. Lu XY. Haung K. Zheng SF. Li BJ. Shi ZJ. Nat. Chem. 2010; 2: 1044
    • 8b Liu W. Cao H. Zhang H. Zhang H. Chung KH. He C. Wang H. Kwong FY. Lei A. J. Am. Chem. Soc. 2010; 132: 16737
    • 8c Shirakawa E. Itoh K. Higashino T. Hayashi T. J. Am. Chem. Soc. 2010; 132: 15537
    • 8d Bhakuni BS. Kumar A. Balkrishna SJ. Sheikh JA. Konar S. Kumar S. Org. Lett. 2012; 14: 11
    • 8e Sharma S. Kumar M. Sharma S. Nayal OS. Kumar N. Singh B. Sharma U. Org. Biomol. Chem. 2016; 14: 8536
    • 9a Nandaluru PR. Bodwell GJ. Org. Lett. 2012; 14: 310
    • 9b Hussain I. Nguyen VT. H. Yawer MA. Dang TT. Fischer C. Reinke H. Langer P. J. Org. Chem. 2007; 72: 6255
    • 9c Prust EE. Carlson EJ. Dahl BJ. Tetrahedron Lett. 2012; 53: 6433
    • 9d Wang Y. Gulevich AV. Gevorgyan V. Chem. Eur. J. 2013; 19: 15836
    • 9e Sun CL. Gu YF. Huang WP. Shi ZJ. Chem. Commun. 2011; 9813
    • 9f Hager A. Mazunin D. Mayer P. Trauner D. Org. Lett. 2011; 13: 1386
    • 9g Thasana N. Worayuthakarn R. Kradanrat P. Hohn E. Young L. Ruchirawat S. J. Org. Chem. 2007; 72: 9379
    • 9h Ceylan S. Klande T. Vogt C. Friese C. Kirschning A. Synlett 2010; 2009
    • 10a Kemperman GJ. Horst BT. Van de Goor D. Roeters T. Bergwerff J. Van der Eem R. Basten J. Eur. J. Org. Chem. 2006; 3169
    • 10b Vishnumurthy K. Makriyannis A. J. Comb. Chem. 2010; 12: 664
    • 10c Luo J. Lu Y. Liu S. Liu J. Deng GJ. Adv. Synth. Catal. 2011; 353: 2604
    • 10d Singha R. Roy S. Nandi S. Ray P. Ray JK. Tetrahedron Lett. 2013; 54: 657
    • 11a Luo S. Luo FX. Zhang XS. Shi ZJ. Angew. Chem. Int. Ed. 2013; 52: 10598
    • 11b Lee TH. Jayakumar J. Cheng CH. Chuang SC. Chem. Commun. 2013; 11797
  • 12 Zhou QJ. Worm K. Dolle RE. J. Org. Chem. 2004; 69: 5147
  • 13 Suárez-Meneses JV. Oukhrib A. Gouygou M. Urrutigoïty M. Daran JC. Cordero-Vargas A. Ortega-Alfarod MC. López-Cortés JG. Dalton Trans. 2016; 9621
    • 14a Hassan J. Sevignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev. 2002; 102: 1359
    • 14b Yu JQ. Shi ZJ. Topics in Current Chemistry . Springer; Berlin: 2010
    • 14c Wu XF. Neumann H. Beller M. Chem. Rev. 2013; 113: 1
    • 14d Yin LX. Liebscher J. Chem. Rev. 2007; 107: 133
    • 15a Djakovitch L. Felpin FX. ChemCatChem 2014; 6: 2175
    • 15b Reay AJ. Fairlamb IJ. S. Chem. Commun. 2015; 16289
    • 15c Santoro S. Kozhushkov SI. Ackermann L. Vaccaro L. Green Chem. 2016; 18: 3471
    • 15d Jafarpour F. Rahiminejadan S. Hazrati H. J. Org. Chem. 2010; 75: 3109
    • 16a Midgley PA. Weyland M. Thomas JM. Gai PL. Boyes ED. Angew. Chem. 2002; 114: 3958
    • 16b Jansson AM. Grøtli M. Halkes KM. Meldal M. Org. Lett. 2002; 4: 27
    • 16c Yuan G. Keane MA. Appl. Catal., B 2004; 52: 301
    • 16d Liebeskind LS. Peña-Cabrera E. Org. Synth. 2000; 77: 138
    • 16e Yu K. Sommer W. Richardson JM. Weck M. Jones CW. Adv. Synth. Catal. 2005; 347: 161
    • 16f Chen JS. Vasiliev AN. Panarello AP. Khinast JG. Appl. Catal., A 2007; 325: 76
    • 17a Heidenreich RG. Kohler K. Krauter JG. E. Pietsch J. Synlett 2002; 1118
    • 17b Conlon DA. Pipik B. Ferdinand S. Leblond CR. Sowa Jr. JR. Izzo B. Collin P. Ho GJ. Williams JM. Shi YJ. Sun Y. Adv. Synth. Catal. 2003; 345: 931
    • 18a Sun MM. Shen GD. Bao WL. Adv. Synth. Catal. 2012; 354: 3468
    • 18b Shen GD. Zhao LY. Wang YC. Xia WF. Yang MS. Zhang TX. RSC Adv. 2016; 6: 84748
    • 18c Shen GD. Yang BC. Huang XQ. Hou YX. Gao H. Cui JC. Cui CS. Zhang TX. J. Org. Chem. 2017; 82: 3798