Download PDF
Synthesis 2022; 54(02): 403-410
DOI: 10.1055/a-1587-8859
paper

Palladium-Catalyzed Butoxycarbonylation of Polybromo(hetero)arenes: A Practical Method for the Preparation of (Hetero)arenepolycarboxylates and -carboxylic Acids

Weilong Wu
a   College of Chemistry and Chemical Engineering and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang, 471934, P. R. of China
,
Yongkang Jing
a   College of Chemistry and Chemical Engineering and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang, 471934, P. R. of China
,
Deyi Zhang
b   College of Chemistry, Zhengzhou University, Zhengzhou, Henan 450001, P. R. of China
,
Xianghe Yan
a   College of Chemistry and Chemical Engineering and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang, 471934, P. R. of China
,
Rong Liang
c   College of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P. R. of China
,
Zhiqiang Lu
a   College of Chemistry and Chemical Engineering and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang, 471934, P. R. of China
,
Baoming Ji  ∗
a   College of Chemistry and Chemical Engineering and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang, 471934, P. R. of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (21372112 and 21801112), the Key Scientific Research Project of Colleges and Universities in Henan Province (19A150004), the General Science Foundation of Henan Province of China (212300410374), and Cultivation Fund of Luoyang Normal University.
› Further Information
    Permissions and Reprints All articles of this category


Abstract

The palladium-catalyzed alkoxycarbonylation of polybromo­(hetero)arenes was investigated systematically. The results show that cheap and readily available in situ Pd(OAc)2/rac-BINAP catalyst can catalyze the butoxycarbonylation of various polybromo(hetero)arenes efficiently, and gave (hetero)arenepolycarboxylates with moderate to high yield (59–94%). Using this method, two new compounds, 4,4′-bis(butoxycarbonyl)-1,1′-bi-2-naphthol and dibutyl [2,2′-bipyrimidine]-5,5′-dicarboxylate, are reported for the first time. In addition, the gram-scale preparation of carboxylate and carboxylic acids was successful performed by butoxycarbonylation followed by hydrolysis. This shows the wide scope of substrates and practical applications of the Pd(OAc)2/rac-BINAP catalytic system. Moreover, these carboxylic acids and carboxylates can be used as ligands or structural units to construct MOFs, metal complexes, and COFs etc.

Key words

polybromoarenes - polybromoheteroarenes - butoxycarbonylation - palladium catalyst - polycarboxylic acid - ligand

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1587-8859.
  • Supporting Information

Primary Data

    Primary data for this article are available online at ­https://zenodo.org/record/5179843 and can be cited using the following DOI: 10.5281/zenodo.5179843.



Publication History

Received: 07 July 2021

Accepted after revision: 16 August 2021

Accepted Manuscript online:
16 August 2021

Article published online:
30 September 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a The Art of Drug Synthesis . Johnson DS, Li JJ. John Wiley & Sons; Hoboken: 2007
      Google Scholar
    • 1b Zapf A, Beller M. Top. Catal. 2002; 19: 101
      Crossref
    • 1c Stetter J, Lieb F. Angew. Chem. Int. Ed. 2000; 39: 1724
      CrossrefPubMed
    • 1d Yang W, Han W, Zhang W, Shan L, Sun J. Synlett 2011; 2253
    • 1e Wang ZQ, Zheng CJ, Fu WJ, Xu C, Wu JS, Ji BM. New J. Chem. 2017; 41: 14152
      Crossref
    • 1f Xu CY, Tang SY, Liu JQ, Deng DS, Ji BM. Chin. J. Struct. Chem. 2017; 36: 127
    • 1g Liu L, Xu CY, Li Y, Wang JC, Zhang YP, Wang JJ. Chin. J. Inorg. Chem. 2017; 33: 1817
    • 1h Liu L, Wang JC, Xu CY, Zhang YQ, Li Y, Li CG, Wang JJ, Zhang YP. J. Mol. Struct. 2019; 1180: 7
      Crossref
    • 1i Zhou Y, Zhang HY, Liu Y. J. Photochem. Photobiol., A 2018; 355: 242
      Crossref
  • 2 Osawa T, Kajitani T, Hashizume D, Ohsumi H, Sasaki S, Takata M, Koizumi Y, Saeki A, Seki S, Fukushima T, Aida T. Angew. Chem. Int. Ed. 2012; 51: 7990
    CrossrefPubMed
  • 3 Rios P, Carter TS, Mooibroek TJ, Crump MP, Lisbjerg M, Pittelkow M, Supekar NT, Boons GJ, Davis AP. Angew. Chem. Int. Ed. 2016; 55: 3387
    CrossrefPubMed
    • 4a Abel AS, Mitrofanov AY, Yakushev AA, Zenkov IS, Morozkov GV, Averin AD, Beletskaya IP, Michalak J, Brandès S, Bessmertnykh-Lemeune A. Asian J. Org. Chem. 2019; 8: 2128
      Crossref
    • 4b Nandi M, Bej S, Ghosh TK, Ghosh P. Chem. Commun. 2019; 55: 3085
      CrossrefPubMed
    • 4c Li J, Liao J, Ren Y, Liu C, Yue C, Lu J, Jiang H. Angew. Chem. Int. Ed. 2019; 58: 17148
      CrossrefPubMed
    • 4d Kreno LE, Leong K, Farha OK, Allendorf M, Van Duyne RP, Hupp JT. Chem. Rev. 2012; 112: 1105
      CrossrefPubMed
    • 4e Cui Y, Chen B, Qian G. Metal-Organic Frameworks for Photonics Applications . Structure and Bonding, Vol. 157. Chen B, Qian G. Springer; Heidelberg: 2014. pp 2
      Google Scholar
    • 4f Müller-Buschbaum K, Beuerle F, Feldmann C. Microporous Mesoporous Mater. 2015; 216: 171
      Crossref
    • 5a Zhu M, Fu WJ, Guo WB, Tian YF, Wang ZQ, Xu C, Ji BM. Eur. J. Org. Chem. 2019; 1614
      Crossref
    • 5b Moriwaki K, Satoh K, Takada M, Ishino Y, Ohno T. Tetrahedron Lett. 2005; 46: 7559
      Crossref
    • 5c Daugulis O, Do HQ, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
      CrossrefPubMed
    • 5d Gooßen LJ, Rodríguez N, Manjolinho F, Lange PP. Adv. Synth. Catal. 2010; 352: 2913
      Crossref
    • 5e Zhu M, Fu W, Guo W, Tian Y, Wang Z, Ji B. Org. Biomol. Chem. 2019; 17: 3374
      CrossrefPubMed
    • 5f Ye M, Gao GL, Edmunds AJ. F, Worthington PA, Morris JA, Yu JQ. J. Am. Chem. Soc. 2011; 133: 19090
      CrossrefPubMed
    • 5g Kochi T, Hamasaki T, Aoyama Y, Kawasaki J, Kakiuchi F. J. Am. Chem. Soc. 2012; 134: 16544
      CrossrefPubMed
    • 5h Hartwig JF. Acc. Chem. Res. 2012; 45: 864
      CrossrefPubMed
    • 5i Rigoli JW, Weatherly CD, Alderson JM, Vo BT, Schomaker JM. J. Am. Chem. Soc. 2013; 135: 17238
      CrossrefPubMed
    • 5j Wertjes WC, Wolfe LC, Waller PJ, Kalyani D. Org. Lett. 2013; 15: 5986
      CrossrefPubMed
    • 5k Ohmura T, Torigoe T, Suginome M. Organometallics 2013; 32: 6170
      Crossref
    • 5l Vasilopoulos A, Zultanski SL, Stahl SS. J. Am. Chem. Soc. 2017; 139: 7705
      CrossrefPubMed
    • 5m Tamura M, Ogata H, Ishida Y, Takahashi Y. Tetrahedron Lett. 2017; 58: 3808
      Crossref
    • 5n Qi L, Hu K, Yu S, Zhu J, Cheng T, Wang X, Chen J, Wu H. Org. Lett. 2017; 19: 218
      CrossrefPubMed
    • 5o Obulesu O, Babu KH, Nanubolu JB, Suresh S. J. Org. Chem. 2017; 82: 2926
      CrossrefPubMed
    • 5p Liao LL, Gui YY, Zhang XB, Shen G, Liu HD, Zhou WJ, Li J, Yu DG. Org. Lett. 2017; 19: 3735
      CrossrefPubMed
    • 6a Chandler CJ, Deady LW, Reiss JA. J. Heterocycl. Chem. 1981; 18: 599
      Crossref
    • 6b Vismara E, Fontana F, Minisci F. Gazz. Chim. Ital. 1987; 117: 135
    • 6c Mattioli M, Mencarelli P. J. Org. Chem. 1990; 55: 776
      Crossref
    • 6d Dupau P, Renouard T, Bozec HL. Tetrahedron Lett. 1996; 37: 7503
      Crossref
    • 6e Li XH, Tjiptoputro AK, Ding J, Xue JM, Zhu YH. Catal. Today 2017; 279: 77
      Crossref
    • 6f Embaby AM, Lelieveldt LP. W. M, Diness PD. F, Meldal PD. M. Chem. Eur J. 2018; 24: 17424
      CrossrefPubMed
    • 6g Puodziukynaite E, Oberst JL, Dyer AL, Reynolds JR. J. Am. Chem. Soc. 2012; 134: 968
      CrossrefPubMed
    • 6h Shigekazu Y. Synth. Commun. 2019; 49: 2210
      Crossref
    • 6i Tanaka K, Oda S, Nishihote S, Hirayama D, Urbanczyk-Lipkowska Z. Tetrahedron: Asymmetry 2009; 20: 2612
      Crossref
    • 7a Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 2. Negishi E, de Meijere A. Wiley; New York: 2002: 2309
      Google Scholar
    • 7b Skoda-Foldes R, Kollar L. Curr. Org. Chem. 2002; 6: 1097
      Crossref
    • 7c Wang L, Neumann H, Spannenberg A, Beller M. Chem. Commun. 2017; 53: 7469
      CrossrefPubMed
    • 7d Sargent BT, Alexanian EJ. J. Am. Chem. Soc. 2016; 138: 7520
      CrossrefPubMed
    • 7e Barnard CF. J. Organometallics 2008; 27: 5402
      Crossref
    • 7f Gross U, Koos P, O’Brien M, Polyzos A, Ley SV. Eur. J. Org. Chem. 2014; 6418
      Crossref
  • 8 Schoenberg A, Heck RF. J. Org. Chem. 1974; 39: 3327
    Crossref
  • 9 Ben-David Y, Portnoy M, Milstein D. J. Am. Chem. Soc. 1989; 111: 8742
    Crossref
    • 10a Beller M, Mägerlein W, Indolese AF, Fischer C. Synthesis 2001; 1098
    • 10b Neumann H, Brennführer A, Groß P, Riermeier T, Almena J, Beller M. Adv. Synth. Catal. 2006; 348: 1255
      Crossref
    • 10c Martinelli JR, Watson DA, Freckmann DM. M, Barder TE, Buchwald SL. J. Org. Chem. 2008; 73: 7102
      CrossrefPubMed
    • 10d Li Y, Xue D, Wang C, Liu ZT, Xiao JL. Chem. Commun. 2012; 48: 1320
      CrossrefPubMed
    • 10e Wan Y, Alterman M, Larhed M, Hallberg A. J. Org. Chem. 2002; 67: 6232
      CrossrefPubMed
  • 11 El-ghayoury A, Ziessel R. J. Org. Chem. 2000; 65: 7757
    CrossrefPubMed
  • 12 Albaneze-Walker J, Bazaral C, Leavey T, Dormer PG, Murry JA. Org. Lett. 2004; 6: 2097
    CrossrefPubMed
    • 13a Huang YL, Zhong DC, Jiang L, Gong YN, Lu TB. Inorg. Chem. 2017; 56: 705
      CrossrefPubMed
    • 13b Coskun A, Hmadeh M, Barin G, Gándara F, Li Q, Choi E, Strutt NL, Cordes DB, Slawin AM. Z, Stoddart JF, Sauvage J.-P, Yaghi OM. Angew. Chem. Int. Ed. 2012; 51: 2160
      CrossrefPubMed
    • 13c Zhang T, Manna K, Lin W. J. Am. Chem. Soc. 2016; 138: 3241
      CrossrefPubMed
    • 13d Thacker NC, Ji P, Lin Z, Urban A, Lin W. Faraday Discuss. 2017; 201: 303
      CrossrefPubMed
    • 13e Manna K, Zhang T, Greene FX, Lin W. J. Am. Chem. Soc. 2015; 137: 2665
      CrossrefPubMed
    • 13f Dehaudt J, Williams NJ, Shkrob IA, Luod H, Dai S. Dalton Trans. 2016; 45: 11624
      CrossrefPubMed
    • 13g Ji BM, Deng DS, Lan HH, Miao SB, Kang GH, Xu CY. Inorg. Chem. Commun. 2017; 81: 15
      Crossref
    • 13h Deng DS, Guo H, Ji BM, Wang WZ, Ma LF, Luo F. New J. Chem. 2017; 41: 12611
      Crossref
  • 14 Chow H, Ng M. Tetrahedron: Asymmetry 1996; 7: 2251
    Crossref
  • 15 Maldonado RR, Zhang X, Hanna S, Gong X, Gianneschi NC, Hupp JT, Farha OK. Dalton Trans. 2020; 49: 6553
    CrossrefPubMed
  • 16 Rybáčková M, Bělohradský M, Holý P, Pohl R, Dekoj V, Závada J. Synthesis 2007; 1554
  • 17 Chiong JA, Zhu J, Bailey JB, Kalaj M, Subramanian RH, Xu W, Cohen SM, Tezcan FA. J. Am. Chem. Soc. 2020; 142: 6907
    CrossrefPubMed
  • 18 Kumar RS, Kumar SK. A, Vijayakrishna K, Sivaramakrishna A, Rao CV. S. B, Sivaraman N, Sahoo SK. Inorg. Chem. 2018; 57: 15270
    CrossrefPubMed
  • 19 Dawar P, Raju MB, Ramakrishna RA. Synth. Commun. 2014; 6: 836
    Crossref
  • 20 Yuan Y, Wu XF. Synlett 2019; 30: 1820
    Article in Thieme Connect
  • 21 Finikova OS, Aleshchenkov SE, Briñas RP, Cheprakov AV, Carroll PJ, Vinogradov SA. J. Org. Chem. 2005; 70: 4617
    CrossrefPubMed
  • 22 Jiang HF, Shen YX, Wang ZY. Tetrahedron Lett. 2007; 48: 7542
    Crossref