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Synlett 2017; 28(19): 2577-2580
DOI: 10.1055/s-0036-1588568
cluster
© Georg Thieme Verlag Stuttgart · New York

Chromium-Catalyzed, Regioselective Cross-Coupling of C–O Bonds by Using Organic Bromides as Reactants

Jinghua Tang
a   Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China
b   Frontier Institute of Science and Technology, Xi’an Jiaotong University, Xi’an 710054, P. R. of China   Email: luomm@scu.edu.cn   Email: zengxiaoming@mail.xjtu.edu.cn
,
Meiming Luo*
a   Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China
,
Xiaoming Zeng  *
a   Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China
b   Frontier Institute of Science and Technology, Xi’an Jiaotong University, Xi’an 710054, P. R. of China   Email: luomm@scu.edu.cn   Email: zengxiaoming@mail.xjtu.edu.cn
› Author AffiliationsWe thank the National Natural Science Foundation of China, SCU, and Beijing National Laboratory for Molecular Sciences for financial support.
Further Information

Publication History

Received: 01 July 2017

Accepted after revision: 22 August 2017

Publication Date:
14 September 2017 (online)

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Published as part of the Cluster C–O Activation

Abstract

We report a chromium-catalyzed cross-coupling of C–O bonds with widely accessible organic bromides as reactants for the preparation of ortho-arylated or -alkylated aromatic aldehydes at room temperature. The use of metallic magnesium is essential for the reaction to occur, giving it an advantage over previous reactions involving Grignard reagents that have to be prepared separately from organic halides before the coupling.

Key words

chromium - C–O activation - cross-coupling - C–C bond formation - organic bromides - regioselectivity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588568.
  • Supporting Information
 

  • References and Notes

  • 1 Johansson Seechurn CC. C. Kitching MO. Colacot TJ. Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
    CrossrefPubMed
  • 2 Metal-Catalyzed Cross-Coupling Reactions . 2nd ed; . de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004
    Google Scholar
  • 3 Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. Vol. 1. Wiley-VCH; Weinheim: 2004
    Google Scholar
  • 4 Wenkert E. Michelotti EL. Swindell CS. J. Am. Chem. Soc. 1979; 101: 2246
    Crossref
  • 5 Cornella J. Zarate C. Martin R. Chem. Soc. Rev. 2014; 43: 8081
    CrossrefPubMed
  • 6 Tobisu M. Chatani N. Acc. Chem. Res. 2015; 48: 1717
    CrossrefPubMed
  • 7 Li B.-J. Yu D.-G. Sun C.-L. Shi Z.-J. Chem. Eur. J. 2011; 17: 1728
    CrossrefPubMed
  • 8 Rosen BM. Quasdorf KW. Wilson DA. Zhang N. Resmerita A.-M. Garg NK. Percec V. Chem. Rev. 2011; 111: 1346
    CrossrefPubMed
  • 9 Tobisu M. Chatani N. Top. Organomet. Chem. 2012; 44: 35
  • 10 Su B. Cao Z.-C. Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
    CrossrefPubMed

      • For selected examples, see:
    • 11a Ohtsuki A. Sakurai S. Tobisu M. Chatani N. Chem. Lett. 2016; 45: 1277
      Crossref
    • 11b Tobisu M. Takahira T. Morioka T. Chatani N. J. Am. Chem. Soc. 2016; 138: 6711
      CrossrefPubMed
    • 11c Nakamura K. Tobisu M. Chatani N. Org. Lett. 2015; 17: 6142
      CrossrefPubMed
    • 11d Tobisu M. Takahira T. Chatani N. Org. Lett. 2015; 17: 4352
      CrossrefPubMed
    • 11e Tobisu M. Morioka T. Ohtsuki A. Chatani N. Chem. Sci. 2015; 6: 3410
      CrossrefPubMed
    • 11f Morioka T. Nishizawa A. Nakamura K. Tobisu M. Chatani N. Chem. Lett. 2015; 44: 1729
      Crossref
    • 11g Tobisu M. Yasutome A. Kinuta H. Nakamura K. Chatani N. Org. Lett. 2014; 16: 5572
      CrossrefPubMed
    • 11h Tobisu M. Yamakawa K. Shimasaki T. Chatani N. Chem. Commun. 2011; 47: 2946
      CrossrefPubMed
    • 11i Tobisu M. Shimasaki T. Chatani N. Chem. Lett. 2009; 38: 710
      Crossref
    • 11j Tobisu M. Shimasaki T. Chatani N. Angew. Chem. Int. Ed. 2008; 47: 4866
      CrossrefPubMed
    • 11k Tobisu M. Takahira T. Ohtsuki A. Chatani N. Org. Lett. 2015; 17: 680
      CrossrefPubMed
  • 12 Dankwardt JW. Angew. Chem. Int. Ed. 2004; 43: 2428
    CrossrefPubMed

      • For selected examples, see:
    • 13a Kondo H. Kochi T. Kakiuchi F. Org. Lett. 2017; 19: 794
      CrossrefPubMed
    • 13b Kondo H. Akiba N. Kochi T. Kakiuchi F. Angew. Chem., Int. Ed. 2015; 54: 9293
      CrossrefPubMed
    • 13c Ogiwara Y. Kochi T. Kakiuchi F. Org. Lett. 2011; 13: 3254
      CrossrefPubMed
    • 13d Ueno S. Mizushima E. Chatani N. Kakiuchi F. J. Am. Chem. Soc. 2006; 128: 16516
      CrossrefPubMed
    • 13e Kakiuchi F. Usui M. Ueno S. Chatani N. Murai S. J. Am. Chem. Soc. 2004; 126: 2706
      CrossrefPubMed

      For selected examples, see:
    • 14a Cao Z.-C. Shi Z.-J. J. Am. Chem. Soc. 2017; 139: 6546
      CrossrefPubMed
    • 14b Zhao F. Zhang Y.-F. Wen J. Yu D.-G. Wei J.-B. Xi Z. Shi Z.-J. Org. Lett. 2013; 15: 3230
      CrossrefPubMed
    • 14c Yu D.-G. Wang X. Zhu R.-Y. Luo S. Zhang X.-B. Wang B.-Q. Wang L. Shi Z.-J. J. Am. Chem. Soc. 2012; 134: 14638
      CrossrefPubMed
    • 14d Yu D.-G. Shi Z.-J. Angew. Chem. Int. Ed. 2011; 50: 7097
      CrossrefPubMed
    • 14e Yu D.-G. Yu M. Guan B.-T. Li B.-J. Zheng Y. Wu Z.-H. Shi Z.-J. Org. Lett. 2009; 11: 3374
      CrossrefPubMed
    • 14f Li B.-J. Xu L. Wu Z.-H. Guan B.-T. Sun C.-L. Wang B.-Q. Shi Z.-J. J. Am. Chem. Soc. 2009; 131: 14656
      CrossrefPubMed
    • 14g Guan B.-T. Wang Y. Li B.-J. Yu D.-G. Shi Z.-J. J. Am. Chem. Soc. 2008; 130: 14468
      CrossrefPubMed
    • 14h Guan B.-T. Xiang S.-K. Wang B.-Q. Sun Z.-P. Wang Y. Zhao K.-Q. Shi Z.-J. J. Am. Chem. Soc. 2008; 130: 3268
      CrossrefPubMed
    • 14i Guan B.-T. Xiang S.-K. Wu T. Sun Z.-P. Wang B.-Q. Zhao K.-Q. Shi Z.-J. Chem. Commun. 2008; 1437
      PubMed

      For selected examples, see:
    • 15a Gu Y. Martin R. Angew. Chem. Int. Ed. 2017; 56: 3187
      CrossrefPubMed
    • 15b Zarate C. Nakajima M. Martin R. J. Am. Chem. Soc. 2017; 139: 1191
      CrossrefPubMed
    • 15c Zarate C. Manzano R. Martin R. J. Am. Chem. Soc. 2015; 137: 6754
      CrossrefPubMed
    • 15d Cornella J. Jackson EP. Martin R. Angew. Chem. Int. Ed. 2015; 54: 4075
      CrossrefPubMed
    • 15e Correa A. Martin R. J. Am. Chem. Soc. 2014; 136: 7253
      CrossrefPubMed
    • 15f Zarate C. Martin R. J. Am. Chem. Soc. 2014; 136: 2236
      CrossrefPubMed
    • 15g Cornella J. Gómez-Bengoa E. Martin R. J. Am. Chem. Soc. 2013; 135: 1997
      CrossrefPubMed
    • 16a Guo L. Liu X. Baumann C. Rueping M. Angew. Chem. Int. Ed. 2016; 55: 15415
      CrossrefPubMed
    • 16b Liu X. Hsiao C.-C. Kalvet I. Leiendecker M. Guo L. Schoenebeck F. Rueping M. Angew. Chem. Int. Ed. 2016; 55: 6093
      CrossrefPubMed

      Rh-catalyzed functionalizations of C–O bonds have been recently disclosed by Chatani and co-workers; see:
    • 18a Tobisu M. Yasui K. Aihara Y. Chatani N. Angew. Chem. Int. Ed. 2017; 56: 1877
      CrossrefPubMed
    • 18b Kinuta H. Tobisu M. Chatani N. J. Am. Chem. Soc. 2015; 137: 1593
      CrossrefPubMed
  • 19 Cong X. Tang H. Zeng X. J. Am. Chem. Soc. 2015; 137: 14367
    CrossrefPubMed
  • 20 Cao Z.-C. Luo Q.-Y. Shi Z.-J. Org. Lett. 2016; 18: 5978
    CrossrefPubMed

      • For examples of cross-coupling reactions using organic halides as reactants mediated by metallic magnesium, see:
    • 21a Czaplik WM. Mayer M. von Wangelin AJ. Angew. Chem. Int. Ed. 2009; 48: 607
      CrossrefPubMed
    • 21b Ilies L. Kobayashi M. Matsumoto A. Yoshikai N. Nakamura E. Adv. Synth. Catal. 2012; 354: 593
      Crossref
    • 21c Liu J.-H. Yang C.-T. Lu X.-Y. Zhang Z.-Q. Xu L. Cui M. Lu X. Xiao B. Fu Y. Liu L. Chem. Eur. J. 2014; 20: 15334
      CrossrefPubMed
    • 21d Li Z. Sun H.-M. Shen Q. Org. Biomol. Chem. 2016; 14: 3314
      CrossrefPubMed
  • 22 o-Arylated Arylcarbaldehydes 3a–m; General Procedure A dried Schlenk tube was charged with (o-methoxyaryl)aldimine 1 (0.2 mmol), Mg (11 mg, 0.44 mmol), and CrCl2 (3 mg, 0.02 mmol). The appropriate aryl bromide 2 (0.4 mmol) was added by a syringe under N2. THF (2 mL) was then added, and the mixture was stirred at r.t. for 12 h. The reaction was quenched with 3 N HCl (1 mL), and the resulting mixture was stirred at r.t. for another 0.5 h and then extracted with EtOAc (3 × 10 mL). The organic layers were combined, dried (Na2SO4), and concentrated under vacuum to give a crude product that was purified by chromatography (silica gel) 1,1′:4′,1′′-Terphenyl-2-carbaldehyde (3b) Prepared by the general procedure from imine 1a (38 mg, 0.2 mmol) and 4-bromobiphenyl (2b). The crude product was purified by column chromatography [silica gel, EtOAc–PE (1:50)] to give a white solid; yield: 39 mg (75%); mp 111–113 °C; IR (neat): 3025, 2961, 2876, 1680, 1594, 1471, 1389, 1250, 1070, 1006, 856, 827 cm–1. 1H NMR (400 MHz, CDCl3): δ = 10.06 (s, 1 H), 8.04 (d, J = 8.0 Hz, 1 H), 7.71–7.65 (m, 5 H), 7.53–7.45 (m, 6 H), 7.37 (t, J = 7.2 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 192.6, 145.7, 141.2, 140.4, 136.8, 133.9, 133.8, 130.9, 130.7, 129.1, 128.0, 127.83, 127.82, 127.3.
  • 23 Shi Z. Glorius F. Chem. Sci. 2013; 4: 829
    Crossref