Synthesis 2021; 53(17): 3029-3036
DOI: 10.1055/a-1416-6997
special topic
Bond Activation – in Honor of Prof. Shinji Murai

Synthesis of Benzo-Fused Cyclic Compounds via Rhodium-Catalyzed Decarboxylative Coupling of Aromatic Carboxylic Acids with Alkynes

Yasuhito Inai
,
Yoshinosuke Usuki
,
Tetsuya Satoh
This work was partly supported by the Japan Society for the Promotion of Science (JSPS) (KAKENHI) (Grant Nos. 20H02745 and 18K19083), and by Osaka City University (OCU) Strategic Research Grant 2020 for basic research to T.S. and the JSPS (KAKENHI) (Grant No. 18H04627) to Y.U.


Abstract

The decarboxylative coupling of diversely substituted benzoic acids with internal alkynes proceeds smoothly in the presence of a [RhCl(cod)]2/1,2,3,4-tetraphenyl-1,3-cyclopentadiene catalyst system to selectively produce highly substituted naphthalene derivatives. The catalyst system is applicable to constructing anthracene and benzo­[c]thiophene frameworks through reactions of naphthoic and thiophene-2-carboxylic acids, respectively.

Supporting Information



Publikationsverlauf

Eingereicht: 17. Februar 2021

Angenommen nach Revision: 08. März 2021

Accepted Manuscript online:
08. März 2021

Artikel online veröffentlicht:
01. April 2021

© 2021. Thieme. All rights reserved

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  • References


    • For representative reviews, see:
    • 1a Wei Y, Hu P, Zhang M, Su W. Chem. Rev. 2017; 117: 8864
    • 1b Font M, Quibell JM, Perry GJ. P, Larrosa I. Chem. Commun. 2017; 53: 5584
    • 1c Drapeau MP, Gooßen LJ. Chem. Eur. J. 2016; 23: 18654
    • 1d Satoh T, Miura M. Synthesis 2010; 3395

      For pioneering work, see:
    • 2a Murai S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N. Nature 1993; 366: 529

    • See also selected reviews on C–H functionalization:
    • 2b Sambiagio C, Schönbauer D, Blieck R, Dao-Huy T, Pototschnig G, Schaaf P, Wiesinger T, Farooq Zia M, Wencel-Delord J, Besset T, Maes BU. W, Schnürch M. Chem. Soc. Rev. 2018; 47: 6603
    • 2c Gulías M, Mascareñas JL. Angew. Chem. Int. Ed. 2016; 55: 11000
    • 2d Chen Z, Wang B, Zhang J, Yu W, Liu Z, Zhang Y. Org. Chem. Front. 2015; 2: 1107
    • 2e Song G, Li X. Acc. Chem. Res. 2015; 48: 1007
    • 2f Ye J, Lautens M. Nat. Chem. 2015; 7: 863
    • 2g Miura M, Satoh T, Hirano K. Bull. Chem. Soc. Jpn. 2014; 87: 751
    • 2h De Sarkar S, Liu W, Kozhushkov SI, Ackermann L. Adv. Synth. Catal. 2014; 356: 1461
    • 2i Wencel-Delord J, Glorius F. Nat. Chem. 2013; 5: 369
    • 2j Colby DA, Tsai AS, Bergman RG, Ellman JA. Acc. Chem. Res. 2012; 45: 814
    • 2k Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
    • 2l Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068
    • 2m Giri R, Shi B.-F, Engle KM, Maugel N, Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242
    • 3a Unoh Y, Hirano K, Satoh T, Miura M. Tetrahedron 2013; 69: 4454
    • 3b Shimizu M, Hirano K, Satoh T, Miura M. J. Org. Chem. 2009; 74: 3478
    • 3c Ueura K, Satoh T, Miura M. Org. Lett. 2007; 9: 1407
    • 4a Hirosawa K, Usuki Y, Satoh T. Adv. Synth. Catal. 2019; 361: 5253
    • 4b Ueura K, Satoh T, Miura M. J. Org. Chem. 2007; 72: 5362

      For homologation reactions of readily available mono-substituted aromatic substrates, see:
    • 5a Wang H, Wang Y, Yang H, Tan C, Jiang Y, Zhao Y, Fu H. Adv. Synth. Catal. 2015; 357: 489
    • 5b Fukutani T, Hirano K, Satoh T, Miura M. J. Org. Chem. 2011; 76: 2867
    • 5c Uto T, Shimizu M, Ueura K, Tsurugi H, Satoh T, Miura M. J. Org. Chem. 2008; 73: 298
    • 5d Yasukawa T, Satoh T, Miura M, Nomura M. J. Am. Chem. Soc. 2002; 124: 12680
    • 5e Kawasaki S, Satoh T, Miura M, Nomura M. J. Org. Chem. 2003; 68: 6836
    • 5f Wu G, Rheingold AL, Feib SL, Heck RF. Organometallics 1987; 6: 1941
    • 5g Sakakibara T, Tanaka Y, Yamasaki T.-I. Chem. Lett. 1986; 797
    • 6a Honjo Y, Shibata Y, Tanaka K. Chem. Eur. J. 2019; 25: 9427
    • 6b Honjo Y, Shibata Y, Kudo E, Namba T, Masutomi K, Tanaka K. Chem. Eur. J. 2018; 24: 317
    • 7a Molotkov AP, Arsenov MA, Kapustin DA, Muratov DV, Shepel’ NE, Fedorov YV, Smol’yakov AF, Knyazeva EI, Lypenko DA, Dmitriev AV, Aleksandrov AE, Maltsev EI, Loginov DA. ChemPlusChem 2020; 85: 334
    • 7b Datsenko VP, Nelyubina YV, Smol’yakov AF, Loginov DA. J. Organomet. Chem. 2018; 874: 7
    • 7c Loginov DA, Konoplev VE. J. Organomet. Chem. 2018; 867: 14
    • 7d Loginov DA, Belova AO, Kudinov AR. Russ. Chem. Bull. 2014; 63: 983

      The catalyst system of [RhCl(cod)]2/C5H2Ph4 has been employed for various dehydrogenative couplings, see:
    • 8a Shimizu M, Tsurugi H, Satoh T, Miura M. Chem. Asian J. 2008; 3: 881
    • 8b Umeda N, Tsurugi H, Satoh T, Miura M. Angew. Chem. Int. Ed. 2008; 47: 4019
    • 8c Mochida S, Shimizu M, Hirano K, Satoh T, Miura M. Chem. Asian J. 2010; 5: 847
  • 9 In contrast, C5H2Ph4 is known to readily coordinate to rhodium, see: Davies DL, Ellul CE, Singh K. J. Organomet. Chem. 2019; 879: 151

    • For example, see:
    • 10a Chávez-González M, Rodríguez-Durán LV, Balagurusamy N, Prado-Barragán A, Rodríguez R, Contreras JC, Aguilar CN. Food Bioprocess Technol. 2012; 5: 445
    • 10b Moodley B, Mulholland DA, Brookes HC. Water SA 2012; 38: 1
    • 10c van Haveren J, Scott EL, Sanders J. Biofuels Bioprod. Bioref. 2008; 2: 41
    • 10d Xu Y, Hanna MA, Isom L. Open Agric. J. 2008; 2: 54
    • 10e Kambourakis S, Draths KM, Frost JW. J. Am. Chem. Soc. 2000; 122: 9042
  • 11 A similar regioselective annulation has been observed in the ruthenium-catalyzed 1:1 coupling of 1n with alkynes, see: Chinnagolla RK, Jeganmohan M. Chem. Commun. 2012; 48: 2030
  • 12 For related selective anthracene construction from 2-naphthaleneboronic acids, see ref. 5b.
  • 13 For the related synthesis of benzo[c]thiophenes from thiophene-2-carbamides, see: Fukuzumi K, Unoh Y, Nishii Y, Satoh T, Hirano K, Miura M. J. Org. Chem. 2016; 81: 2474
    • 14a Novák Z, Nemes P, Kotschy A. Org. Lett. 2004; 6: 4917
    • 14b Moon J, Jang M, Lee S. J. Org. Chem. 2008; 74: 1403
    • 14c Hein SJ, Arslan H, Keresztes I, Dichtel WR. Org. Lett. 2014; 16: 4416
  • 15 Peng S, Sun Z, Zhu H, Chen N, Sun X, Gong X, Wang J, Wang L. Org. Lett. 2020; 22: 3200
  • 16 Wu YT, Huang K.-H, Shin C.-C, Wu T.-C. Chem. Eur. J. 2008; 14: 6697