Download PDF
Synlett 2023; 34(11): 1280-1284
DOI: 10.1055/a-2007-2958
letter

Ligand-Free Palladium-Catalyzed Substoichiometric Base ­Mediated Carbonylation of Aryl Iodides with Alkenylboronic Acids under Ambient Conditions

Lili Tang‡
a   Hunan Engineering Research Center for Recycled Aluminum, College of Chemistry and Materials Engineering, Huaihua University, Huaihua 418008, P. R. of China
,
Yanqun Gao‡
b   Jiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing 210023, P. R. of China
,
Junjie Chen
b   Jiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing 210023, P. R. of China
,
Linlin Yang
b   Jiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing 210023, P. R. of China
,
Bing Xiao
b   Jiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing 210023, P. R. of China
,
Ge Shen
b   Jiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing 210023, P. R. of China
,
Yuejun Ouyang∗
a   Hunan Engineering Research Center for Recycled Aluminum, College of Chemistry and Materials Engineering, Huaihua University, Huaihua 418008, P. R. of China
,
Wei Han  ∗
b   Jiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing 210023, P. R. of China
› Author AffiliationsThe work was sponsored by the Natural Science Foundation of Hunan Province (2020JJ4487, 2020JJ4073), the Qing Lan Project Young and Middle-Aged Academic Leaders of Jiangsu Provincial Colleges and Universities, and the Priority Academic Program Development of Jiangsu Higher Education Institutions.
› Further Information
    Permissions and Reprints All articles of this category


Abstract

A highly efficient, practical, and ligand-free palladium-catalyzed carbonylation of aryl iodides with alkenylboronic acids has been developed. A variety of chalcones and α-branched enones were isolated in satisfactory to good yields with good substrate compatibilities under an ambient pressure of CO at room temperature. Moreover, the transformation proceeds well in the presence of a substoichiometric amount of base. The merit of this strategy as a late-stage functionalization platform has been demonstrated by modifications of complex substrates derived from estrone and 3-phenyl-l-alanine.

Key words

palladium catalysis - carbonylation - aryl iodides - alkenylboronic acids - chalcones - enones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2007-2958.
  • Supporting Information


Publication History

Received: 05 December 2022

Accepted after revision: 04 January 2023

Accepted Manuscript online:
04 January 2023

Article published online:
02 February 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References and Notes

    • 1a Zhuang C, Zhang W, Sheng C, Zhang W, Xing C, Miao Z. Chem. Rev. 2017; 117: 7762
      CrossrefPubMed
    • 1b Damazio RG, Zanatta AP, Cazarolli LH, Chiaradia LD, Mascarello A, Nunes RJ, Yunes RA, Barreto Silva FR. M. Eur. J. Med. Chem. 2010; 45: 1332
      CrossrefPubMed
    • 1c Das U, Doroudi A, Gul HI, Pati HN, Kawase M, Sakagami H, Chu Q, Stables JP, Dimmock JR. Bioorg. Med. Chem. 2010; 18: 2219
      CrossrefPubMed
    • 1d Grealis JP, Müller-Bunz H, Ortin Y, Casey M, McGlinchey MJ. Eur. J. Org. Chem. 2013; 332
      Crossref
    • 1e Juvale K, Pape VF. S, Wiese M. Bioorg. Med. Chem. 2012; 20: 346
      CrossrefPubMed
    • 1f Leow P.-C, Bahety P, Boon CP, Lee CY, Tan KL, Yang T, Ee P.-LR. Eur. J. Med. Chem. 2014; 71: 67
      CrossrefPubMed
    • 2a Elkanzi NA. A, Hrichi H, Alolayan RA, Derafa W, Zahou FM, Bakr RB. ACS Omega 2022; 7: 27769
      CrossrefPubMed
    • 2b Claisen L, Claparède A. Ber. Dtsch. Chem. Ges. 1881; 14: 2460
      Crossref
    • 2c Schmidt JG. Ber. Dtsch. Chem. Ges. 1881; 14: 1459
      Crossref
    • 2d Niu C, Tuerxuntayi A, Li G, Kabas M, Dong C.-Z, Aisa HA. Chin. Chem. Lett. 2017; 28: 1533
      Crossref
    • 2e Mukaiyama T. Org. React. (N. Y.) 1982; 28: 203
      Crossref
    • 2f Zhong Q, Rongjian L. Yingyong Huaxue 1990; 7: 89
    • 2g Iranpoor N, Kazemi F. Tetrahedron 1998; 54: 9475
      Crossref
    • 2h Nakano T, Irifune S, Umano S, Inada A, Ishii Y, Ogawa M. J. Org. Chem. 1987; 52: 2239
      Crossref
    • 2i Si ZK, Zhang Q, Xue ZM, Zhu YY, Ming L, Sheng QR, Liu YG. Chin. Chem. Lett. 2011; 22: 1025
      Crossref
    • 2j Kwon MS, Kim N, Seo SH, Park IS, Cheedrala RK, Park J. Angew. Chem. Int. Ed. 2005; 44: 6913
      CrossrefPubMed
    • 2k Yamada YM. A, Uozumi Y. Tetrahedron 2007; 63: 8492
      Crossref
    • 3a Zhang S, Neumann H, Beller M. Chem. Soc. Rev. 2020; 49: 3187
      CrossrefPubMed
    • 3b Ning Y, Ohwada T, Chen F.-E. Green Synth. Catal. 2021; 2: 247
      Crossref
    • 3c Carbon Monoxide in Organic Synthesis: Carbonylation Chemistry. Gabriele B. Wiley-VCH; Weinheim: 2021
      Google Scholar
    • 3d Beller M, Eckert M. Angew. Chem. Int. Ed. 2000; 39: 1010
      CrossrefPubMed
    • 3e Lu S.-M, Alper H. J. Am. Chem. Soc. 2005; 127: 14776
      CrossrefPubMed
    • 3f Jacobi von Wangelin A, Neumann H, Beller M. In Catalytic Carbonylation Reactions . Beller M. Springer-Verlag; Berlin: 2006: 207
      CrossrefGoogle Scholar
    • 3g Brennführer A, Neumann H, Beller M. Angew. Chem. Int. Ed. 2009; 48: 4114
      CrossrefPubMed
    • 3h Wu X.-F, Neumann H, Beller M. Chem. Soc. Rev. 2011; 40: 4986
      CrossrefPubMed
    • 3i Liu Q, Zhang H, Lei A. Angew. Chem. Int. Ed. 2011; 50: 10788
      CrossrefPubMed
    • 3j Gabriele B, Mancuso R, Salerno G. Eur. J. Org. Chem. 2012; 6825
      Crossref
    • 3k Sumino S, Fusano A, Fukuyama T, Ryu I. Acc. Chem. Res. 2014; 47: 1563
      CrossrefPubMed
    • 3l Peng J.-B, Geng H.-Q, Wu X.-F. Chem 2019; 5: 526
      Crossref
    • 3m Peng J.-B, Wu F.-P, Wu X.-F. Chem. Rev. 2019; 119: 2090
      CrossrefPubMed
    • 3n Friis SD, Lindhardt AT, Skrydstrup T. Acc. Chem. Res. 2016; 49: 594
      CrossrefPubMed
    • 3o Xu F, Han W. Youji Huaxue 2018; 38: 2519
    • 4a Wu X.-F, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 5284
      CrossrefPubMed
    • 4b Wu X.-F, Neumann H, Spannenberg A, Schulz T, Jiao H, Beller M. J. Am. Chem. Soc. 2010; 132: 14596
      CrossrefPubMed
    • 4c Wu X.-F, Neumann H, Beller M. Chem. Asian J. 2012; 7: 282
      CrossrefPubMed
    • 4d Sumino S, Ui T, Hamada Y, Fukuyama T, Ryu I. Org. Lett. 2015; 17: 4952
      CrossrefPubMed
    • 4e Gøgsig TM, Nielsen DU, Lindhardt AT, Skrydstrup T. Org. Lett. 2012; 14: 2536
      CrossrefPubMed
    • 4f Hermange P, Gøgsig TM, Lindhardt AT, Taaning RH, Skrydstrup T. Org. Lett. 2011; 13: 2444
      CrossrefPubMed
  • 5 Zhang Z, Liu Y, Gong M, Zhao X, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2010; 49: 1139
    CrossrefPubMed
  • 6 Geng H.-Q, Wang L.-C, Hou C.-Y, Wu X.-F. Org. Lett. 2020; 22: 1160
    CrossrefPubMed
  • 7 Yang Z, Gong P.-X, Chen J, Zhang J, Gong X, Han W. Synlett 2021; 32: 1207
    Article in Thieme ConnectPubMed
    • 8a Zhao H, Du H, Yuan X, Wang T, Han W. Green Chem. 2016; 18: 5782
      Crossref
    • 8b Xu F, Li D, Han W. Green Chem. 2019; 21: 2911
      Crossref
    • 8c Jin F, Han W. Chem. Commun. 2015; 51: 9133
      CrossrefPubMed
    • 8d Zhong Y, Han W. Chem. Commun. 2014; 50: 3874
      CrossrefPubMed
    • 8e Yu D, Xu F, Li D, Han W. Adv. Synth. Catal. 2019; 361: 3102
      Crossref
    • 8f Zhou Q, Wei S, Han W. J. Org. Chem. 2014; 79: 1454
      CrossrefPubMed
    • 8g Zhong Y, Gong X, Zhu X, Ni Z, Wang H, Fu J, Han W. RSC Adv. 2014; 4: 63216
      Crossref
    • 8h Han W, Liu B, Chen J, Zhou Q. Synlett 2017; 28: 835
      Article in Thieme Connect
    • 8i Cheng L, Zhong Y, Ni Z, Du H, Jin F, Rong Q, Han W. RSC Adv. 2014; 4: 44312
      Crossref
  • 9 Poly(ethylene glycol) (PEG) is often used as a good phase-transfer agent. This property favors gas–liquid–solid multiphase catalytic reactions. Additionally, PEG is a highly polar solvent that is capable of strongly solvating polar molecules such as carbon monoxide to reduce mass-transfer resistance. These two positive properties probably permit PEG to show excellent performance in the current transformation. For a review, see: Chen J, Spear SK, Huddleston JG, Rogers RD. Green Chem. 2005; 7: 64
    Crossref
  • 10 Littke AF, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 4176
    CrossrefPubMed
  • 11 Ye J, Zhao J, Xu J, Mao Y, Zhang YJ. Chem. Commun. 2013; 49: 9761
    CrossrefPubMed
    • 12a Han W, Liu C, Jin Z.-L. Org. Lett. 2007; 9: 4005
      CrossrefPubMed
    • 12b Han W, Liu C, Jin Z.-L. Adv. Synth. Catal. 2008; 350: 501
      Crossref
  • 13 (2E)-1-(4-Nitrophenyl)-3-phenylprop-2-en-1-one (3aa): Typical Procedure A 25-mL flask was charged with Pd(OAc)2 (0.005 mmol, 1.2 mg), 1-iodo-4-nitrobenzene (1a; 0.25 mmol, 62.9 mg), (E)-styrylboronic acid (2a; 0.30 mmol, 45.8 mg), Na2CO3 (0.125 mmol, 13.3 mg), PivOH (0.125 mmol, 13.2 mg), and PEG-400 (2.0 g), then subjected to several standard cycles of evacuation and backfilling with pure dry CO. The mixture was then stirred at RT and atmospheric pressure for 3 h. When the reaction was complete, the mixture was extracted with Et2O (3 × 15 mL). The organic phases were combined, and the volatile components were evaporated under reduced pressure. The crude product was purified by column chromatography [silica gel, PE–Et2O (100:1 to 10:1)] to give a yellow solid; yield: 59 mg (94%, E/Z > 99:1); mp 143–144 °C. 1H NMR (400 MHz, CDCl3): δ = 8.37 (d, J = 8.8 Hz, 2 H), 8.17 (d, J = 8.8 Hz, 2 H), 7.88 (d, J = 15.6 Hz, 1 H), 7.69–7.67 (m, 2 H), 7.51 (d, J = 15.6 Hz, 1 H), 7.48–7.45 (m, 3 H). 13C NMR (100 MHz, CDCl3): δ = 189.0, 150.0, 146.8, 143.0, 134.3, 131.2, 129.4, 129.1, 128.7, 123.8, 121.2.