Synthesis 2018; 50(06): 1315-1322
DOI: 10.1055/s-0036-1591524
paper
© Georg Thieme Verlag Stuttgart · New York

N-Heterocyclic Carbene (NHC)-Catalyzed One-Pot Aerobic Oxidative Synthesis of 2-Substituted Benzo[d]oxazoles, Benzo[d]thiazoles and 1,2-Disubstituted Benzo[d]imidazoles

Quan Zhou
a   Department of Chemistry, Fudan University, 220 Handan Rd., Shanghai 200433, P. R. of China   Email: xfhou@fudan.edu.cn
,
Shu Liu
b   Technical Center for Industrial Product and Raw Material Inspection and Testing, Shanghai Entry-Exit Inspection and Quarantine Bureau, Shanghai 200135, P. R. of China
,
Ming Ma
b   Technical Center for Industrial Product and Raw Material Inspection and Testing, Shanghai Entry-Exit Inspection and Quarantine Bureau, Shanghai 200135, P. R. of China
,
He-Zhen Cui
a   Department of Chemistry, Fudan University, 220 Handan Rd., Shanghai 200433, P. R. of China   Email: xfhou@fudan.edu.cn
,
Xi Hong
a   Department of Chemistry, Fudan University, 220 Handan Rd., Shanghai 200433, P. R. of China   Email: xfhou@fudan.edu.cn
,
Shuang Huang
a   Department of Chemistry, Fudan University, 220 Handan Rd., Shanghai 200433, P. R. of China   Email: xfhou@fudan.edu.cn
,
Jing-Fan Zhang
a   Department of Chemistry, Fudan University, 220 Handan Rd., Shanghai 200433, P. R. of China   Email: xfhou@fudan.edu.cn
,
a   Department of Chemistry, Fudan University, 220 Handan Rd., Shanghai 200433, P. R. of China   Email: xfhou@fudan.edu.cn
› Author Affiliations
We are grateful for the financial support by the National Science Foundation of China (Grant No. 21271047), General Administration of Quality Supervision, Inspection and Quarantine of China (No. 2015IK217, 2016IK225), and ShanXi Science and Technology Department, China (Project No. MH2014-07).
Further Information

Publication History

Received: 18 October 2017

Accepted after revision: 24 November 2017

Publication Date:
20 December 2017 (online)


Abstract

N-Heterocyclic carbene (NHC), generated in situ from easily available N-heterocyclic imidazolium salt with air as terminal oxidant, has successfully been utilized as a cheap and efficient catalyst for one-pot aerobic oxidative synthesis of 2-arylbenzo[d]oxazoles, 2-substituted benzo[d]thiazoles, and 1,2-disubstituted benzo[d]imidazoles.

Supporting Information

 
  • References

    • 1a Comprehensive Heterocyclic Chemistry III . Vol. 4. Katritzky AR. Ramsden CA. Scriven EF.V. Taylor RJ. K. Elsevier; Amsterdam: 2008
    • 1b Katritzky AR. Pozharskii AF. Handbook of Heterocyclic Chemistry . 2nd ed. Pergamon; Oxford: 2000
  • 2 Carvalho LC. Eduarda F. Marques MB. Chem. Eur. J. 2011; 17: 12544 ; and references cited therein
    • 3a Cui M. Ono M. Kimura H. Ueda M. Nakamoto Y. Togashi K. Okamoto Y. Ihara M. Takahashi R. Liu B.-L. Saji H. J. Med. Chem. 2012; 55: 9136
    • 3b Noёl S. Cadet S. Gras E. Hureau C. Chem. Soc. Rev. 2013; 42: 7747
    • 4a Huo H. Harmsand K. Meggers E. J. Am. Chem. Soc. 2016; 138: 6936
    • 4b Huo H.-H. Wang C.-Y. Harms K. Meggers E. J. Am. Chem. Soc. 2015; 137: 9551
    • 4c Huo H.-H. Fu C. Harmsa K. Meggers E. J. Am. Chem. Soc. 2014; 136: 2990

      For selected examples for transition-metal-catalyzed cross-coupling, see:
    • 5a Ueda S. Nagasawa H. J. Org. Chem. 2009; 74: 4272
    • 5b Ueda S. Nagasawa H. Angew. Chem. Int. Ed. 2008; 47: 6411
    • 5c Shibahara F. Yamaguchi E. Murai T. Chem. Commun. 2010; 46: 2471
    • 5d Yan X.-M. Mao X.-R. Huang Z.-Z. Heterocycles 2011; 83: 1371
    • 5e Shen X.-B. Zhang Y. Chen W.-X. Xiao Z.-K. Hu T.-T. Shao L.-X. Org. Lett. 2014; 16: 1984
    • 5f Muto K. Yamaguchi J. Lei A. Itami K. J. Am. Chem. Soc. 2013; 135: 16384
    • 5g Zhu F. Tao J.-L. Wang Z.-X. Org. Lett. 2015; 17: 4926
    • 5h Do H.-Q. Daugulis O. J. Am. Chem. Soc. 2007; 129: 12404
    • 5i Hachiya H. Hirano K. Satoh T. Miura M. Angew. Chem. Int. Ed. 2010; 49: 2202
    • 5j Garduño JA. García JJ. ACS Catal. 2015; 5: 3470
    • 5k Wu Q. Chen Y. Yan D. Zhang M. Lu Y. Sun W.-Y. Zhao J. Chem. Sci. 2017; 8: 169
    • 5l Li B. Lan J. Wu D. You J. Angew. Chem. Int. Ed. 2015; 54: 14008
    • 5m Ackermann L. Barfüsser S. Pospech J. Org. Lett. 2010; 12: 724
  • 6 Viirre RD. Evindar G. Batey RA. J. Org. Chem. 2008; 73: 3452 ; and references cited therein
    • 7a Terashima M. Ishii M. Kanaoka Y. Synthesis 1982; 484
    • 7b Bourgrin K. Loupy A. Soufiaoui M. Tetrahedron 1998; 54: 8055
    • 7c Pottorf RS. Chadha NK. Katkevics M. Ozola V. Suna E. Ghane H. Regberg T. Player MR. Tetrahedron Lett. 2003; 44: 175

      For oxidative cyclization synthesis, see:
    • 8a Chang J. Zhao K. Pan S. Tetrahedron Lett. 2002; 43: 951
    • 8b Varma RS. Saini RK. Prakash O. Tetrahedron Lett. 1997; 38: 2621
    • 8c Praveen C. Kumar KH. Muralidharan D. Perumal PT. Tetrahedron 2008; 64: 2369
    • 8d Srivastava RG. Venkataramani PS. Synth. Commun. 1988; 18: 1537
    • 8e Bardajee GR. Mohammadi M. Kakavand N. Appl. Organomet. Chem. 2016; 30: 51

      For dehydrogenative coupling reaction of benzyl alcohols with 2-aminophenol or derivatives, see:
    • 9a Shi X. Guo J. Liu J. Ye M. Xu Q. Chem. Eur. J. 2015; 21: 9988
    • 9b Khalafi-Nezhad A. Panahi F. ACS Catal. 2014; 4: 1686
    • 9c Shiraishi Y. Sugano Y. Tanaka S. Hirai T. Angew. Chem. Int. Ed. 2010; 49: 1656
    • 9d Blacker AJ. Farah MM. Hall MI. Marsden SP. Saidi O. Williams JM. J. Org. Lett. 2009; 11: 2039
  • 10 Kawashita Y. Nakamichi N. Kawabata H. Hayashi M. Org. Lett. 2003; 5: 3713
    • 11a Kidwai M. Bansal V. Saxena A. Aerryb S. Mozumdar S. Tetrahedron Lett. 2006; 47: 8049
    • 11b Maleki B. Baghayeri M. Vahdat SM. Mohammadzadeh A. Akhoondi S. RSC Adv. 2015; 5: 46545
    • 11c Khalafi-Nezhad A. Panahi F. Yousefi R. J. Iran. Chem. Soc. 2014; 11: 1311
    • 11d Tang L. Guo X. Yang Y. Zha Z. Wang Z. Chem. Commun. 2014; 50: 6145
    • 11e Banerjee S. Payra S. Saha A. Sereda G. Tetrahedron Lett. 2014; 55: 5515
    • 11f Sharma H. Singh N. Jang DO. Green Chem. 2014; 16: 4922
    • 11g Yang D. Zhu X. Wei W. Sun N. Yuan L. Jiang M. You J. Wang H. RSC Adv. 2014; 4: 17832
    • 11h Brahmachari G. Laskar S. Barik P. RSC Adv. 2013; 3: 14245
    • 11i Yang D. Liu P. Zhang N. Wei W. Yue M. You J. Wang H. ChemCatChem 2014; 6: 3434
    • 12a Fan X. He Y. Zhang X. Wang J. Chin. J. Chem. 2011; 29: 773
    • 12b Bala M. Verma PK. Sharm U. Kumar N. Singh B. Green Chem. 2013; 15: 1687
    • 13a Chen Y.-X. Qian L.-F. Zhang W. Han B. Angew. Chem. Int. Ed. 2008; 47: 9330
    • 13b Yu J. Lu M. J. Chin. Chem. Soc. 2014; 61: 578
    • 14a Cho YH. Lee C.-Y. Ha D.-C. Cheon C.-H. Adv. Synth. Catal. 2012; 354: 2992
    • 14b Reyes H. Heltran IH. Rivera-Becerril E. Tetrahedron Lett. 2011; 52: 308
    • 14c Cho Y.-H. Lee C.-Y. Cheon C.-H. Tetrahedron 2013; 69: 6565
    • 15a Bala M. Verma PK. Sharma D. Kumar N. Singh B. Mol. Divers. 2015; 19: 263
    • 15b Bachhav HM. Bhagat SB. Telvekar VN. Tetrahedron Lett. 2011; 52: 5697

      For reviews on NHC-organocatalysis, see:
    • 16a Vair V. Vellalath S. Babu BP. Chem. Soc. Rev. 2008; 37: 2691
    • 16b Flanigan DM. Romanov-Michailidis FN. White A. Rovis T. Chem. Rev. 2015; 115: 9307
    • 16c Marion N. Díez-González S. Nolan SP. Angew. Chem. Int. Ed. 2007; 46: 2988
    • 16d Menon RS. Bijub AT. Nair V. Chem. Soc. Rev. 2015; 44: 5040
    • 16e Bugaut X. Glorius F. Chem. Soc. Rev. 2012; 41: 3511
    • 16f Zhong R. Lindhorst AC. Groche FJ. Kühn FE. Chem. Rev. 2017; 117: 1970
    • 16g Tang W. Du D. Chem. Rec. 2016; 16: 1489
    • 16h Zhang C. Hooper JF. Lupton DW. ACS Catal. 2017; 7: 2583

      For recent reports on NHC catalyzed reactions with various oxidants, see: Air/O2:
    • 17a Ta L. Axelsson A. Sunden H. Green Chem. 2016; 18: 686
    • 17b Meng J.-J. Gao M. Wei Y.-P. Zhang W.-Q. Chem. Asian J. 2012; 7: 872
    • 17c Denk MK. Milutinović NS. Marczenko KM. Sadowski NM. Paschos A. Chem. Sci. 2017; 8: 1883
    • 17d Wang G. Fu Z. Huang W. Org. Lett. 2017; 19: 3362
    • 17e Youn SW. Yoo HJ. Adv. Synth. Catal. 2017; 359: 2176
    • 17f Wang G. Chen X. Miao G. Yao W. Ma C. J. Org. Chem. 2013; 78: 6223

    • Quinone:
    • 17g Zheng C. Liu X. Ma C. J. Org. Chem. 2017; 82: 6940
    • 17h Axelsson A. Hammarvid E. Ta L. Sundén H. Chem. Commun. 2016; 52: 11571
    • 17i Lu Y. Tang W. Zhang Y. Du D. Lu T. Adv. Synth. Catal. 2013; 355: 321
    • 17j Sarkar SD. Grimme S. Studer A. J. Am. Chem. Soc. 2010; 132: 1190
    • 17k Biswas A. De SS. Fröhlich R. Studer A. Org. Lett. 2011; 13: 4966
    • 17l Zhu T. Mou C. Li B. Smetankova M. Song B.-A. Chi YR. J. Am. Chem. Soc. 2015; 137: 5658
    • 17m Wanner B. Mahatthananchai J. Bode JW. E. Org. Lett. 2011; 13: 5378
    • 17n Mahatthananchai J. Bobe JW. Acc. Chem. Res. 2014; 47: 696
    • 17o Finney EE. Ogawa KA. Boydston AJ. J. Am. Chem. Soc. 2012; 134: 12374
    • 18a Cao H. Zhu X.-H. Wang D. Sun Z. Deng Y. Hou X.-F. Zhao D. ACS Catal. 2015; 5: 27
    • 18b Zou Q. Wang Y.-N. Guo X.-Q. Zhu X.-H. Li Z.-M. Hou X.-F. Organometallics 2015; 34: 1021
    • 18c Guo X.-Q. Wang Y.-N. Wang D. Cai L.-H. Chen Z.-X. Hou X.-F. Dalton Trans. 2012; 41: 14557
    • 18d Guo X.-Q. Wang C.-X. Wang Y.-N. Zhong R. Zhu X.-H. Cai L.-H. Gao Z.-W. Hou X.-F. Adv. Synth. Catal. 2013; 355: 1117
  • 19 Zhou Q. Zhang J.-F. Cao H. Zhong R. Hou X.-F. J. Org. Chem. 2016; 81: 12169
  • 20 Zhong R. Wang Y.-N. Guo X.-Q. Hou X.-F. J. Organomet. Chem. 2011; 696: 1703
    • 21a Hugar KM. Kostalik HA. Coates GW. J. Am. Chem. Soc. 2015; 137: 8730
    • 21b Denk MK. Rodezno JM. Gupta S. Lough AJ. J. Organomet. Chem. 2001; 617–618: 242
  • 22 Chang A. Scheidt KA. J. Am. Chem. Soc. 2006; 128: 4558
    • 23a CCDC 1562002 (3cc′) 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.
    • 23b Jorapur YR. Rajagopal G. Saikia P. Pal RR. Tetrahedron Lett. 2008; 49: 1495
  • 24 Zhang G. Liu C. Yi H. Meng Q. Bian C. Chen H. Jian J.-X. Wu L.-Z. Lei A. J. Am. Chem. Soc. 2015; 137: 9273
    • 25a Zhang C. Zhang L. Jiao N. Green Chem. 2012; 14: 3273
    • 25b Lee Y.-S. Cho Y.-H. Lee S. Bin J.-K. Yang J. Chae G. Cheon C.-H. Tetrahedron 2015; 71: 532
  • 26 Cui L. Xiao S. Yang H. Xu P. Chen F. Li Z. Liang R. Xia Z. Chin. J. Org. Chem. 2011; 31: 672

    • For regiodefined 1,2-disubstituted benzo[d]imidazole synthesis, see:
    • 27a Kommi DN. Kumar D. Bansal R. Chebolu R. Chakraborti AK. Green Chem. 2012; 14: 3329
    • 27b Baars H. Beyer A. Kohlhepp SV. Bolm C. Org. Lett. 2014; 16: 536
    • 27c Carvalho LC. R. Fernandes E. Marques MM. B. Chem. Eur. J. 2011; 17: 12544 ; and references cited therein
  • 28 Initially, BuCl, BuBr, and BuI were chosen as in situ alkylation reagent; however, n-BuCl and n-BuBr were not suitable due to their lower boiling point than the reaction temperature.
  • 29 Wang L. Ma Z.-G. Wei X.-J. Meng Q.-Y. Yang D.-T. Du S.-F. Chen Z.-F. Wu L.-Z. Liu Q. Green Chem. 2014; 16: 3752
  • 30 Wang J. Liu C. Yuan J. Lei A. Angew. Chem. Int. Ed. 2013; 52: 2256
  • 31 After the Schiff base had mostly formed the oxidative cyclization product, the carbene could slowly deteriorate through routine hydrolysis and ring-opening with trace moisture in the open-air reaction system, see ref. 21b.
    • 32a Wu G. Zhou J. Zhang M. Hu P. Su W. Chem. Commun. 2012; 48: 8964
    • 32b Haugwitz RD. Angel RG. Jacobs GA. Maurer BV. Narayanan VL. Cruthers LR. Szanto J. J. Med. Chem. 1982; 25:  969
    • 32c McCallum T. Barriault L. Chem. Sci. 2016; 7: 4754
    • 32d Mayo MS. Yu X. Zhou X. Yamamoto XY. Bao M. Org. Lett. 2014; 16: 764
    • 32e Nguyen KM. H. Largeron M. Eur. J. Org. Chem. 2016; 1025
    • 32f Song B. Knauber T. Gooßen LJ. Angew. Chem. Int. Ed. 2013; 52: 2954