Pd-Catalyzed Activation of Carbon-Carbon Bonds in Hydroxymethylfurfural Derivatives.
C−C activation
green chemistry
homogeneous catalysis
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
23 Oct 2023
23 Oct 2023
Historique:
received:
13
07
2023
pubmed:
14
7
2023
medline:
14
7
2023
entrez:
14
7
2023
Statut:
ppublish
Résumé
Palladium-catalyzed activation of C-C bonds in organic molecules is a powerful tool for the synthesis of value-added compounds. 5-Hydroxymethylfurfural (HMF) derivatives are a promising class of biomass-derived chemicals that have received considerable attention due to their potential applications in the synthesis of biologically active molecules and materials. However, the selective activation of unstrained C-C bonds is a challenging task, mainly due to their relatively high bond dissociation energies. Herein, we report a palladium-catalyzed method for the efficient C-C bond activation of HMF derivatives, enabling their arylation with iodobenzenes. Mechanistic studies, including reaction-profile analysis, competition experiments and head-space IR spectroscopy suggest a decarboxylative mechanism.
Identifiants
pubmed: 37449730
doi: 10.1002/chem.202302038
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202302038Subventions
Organisme : Fonds der Chemischen Industrie
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
For hydroxymethylfurfural as a building-block see:
F. W. Lichtenthaler, Acc. Chem. Res. 2002, 35, 728-737;
X. Tong, Y. Ma, Y. Li, Appl. Catal. A 2010, 385, 1-13;
O. O. James, S. Maity, L. A. Usman, K. O. Ajanaku, O. O. Ajani, T. O. Siyanbola, S. Sahu, R. Chaubey, Energy Environ. Sci. 2010, 3, 1833;
A. A. Rosatella, S. P. Simeonov, R. F. M. Frade, C. A. M. Afonso, Green Chem. 2011, 13, 754;
R. Karinen, K. Vilonen, M. Niemelä, ChemSusChem 2011, 4, 1002-1016;
L. Hu, G. Zhao, W. Hao, X. Tang, Y. Sun, L. Lin, S. Liu, RSC Adv. 2012, 2, 11184;
R.-J. van Putten, J. C. van der Waal, E. de Jong, C. B. Rasrendra, H. J. Heeres, J. G. de Vries, Chem. Rev. 2013, 113, 1499-1597;
R. A. Sheldon, Green Chem. 2014, 16, 950-963;
L. Hu, L. Lin, Z. Wu, S. Zhou, S. Liu, Renewable Sustainable Energy Rev. 2017, 74, 230-257;
L. T. Mika, E. Cséfalvay, Á. Németh, Chem. Rev. 2018, 118, 505-613;
R. Palkovits, Chem. Ing. Tech. 2018, 90, 1699-1708;
B. Wozniak, S. Tin, J. G. de Vries, Chem. Sci. 2019, 10, 6024-6034;
J. Esteban, A. J. Vorholt, W. Leitner, Green Chem. 2020, 22, 2097-2128;
D. Qu, S. He, L. Chen, Y. Ye, Q. Ge, H. Cong, N. Jiang, Y. Ha, Front. Chem. 2022, 10, 10.3389/fchem.2022.1055865;
D. J. Aranha, P. R. Gogate, Ind. Eng. Chem. Res. 2023, 62, 3053-3078;
W. Zhang, H. Qian, Q. Hou, M. Ju, Green Chem. 2023, 25, 893-914;
Theerthagiri, K. Karuppasamy, J. Park, N. Rahamathulla, M. L. A. Kumari, M. K. R. Souza, E. S. F. Cardoso, A. P. Murthy, G. Maia, H.-S. Kim, M. Y. Choi, Environ. Chem. Lett. 2023, 21, 1555-1583.
For C−C bond activation see:
G. Dong, C−C Bond Activation, Springer, Berlin, Heidelberg, 2014;
C.-H. Jun, Chem. Soc. Rev. 2004, 33, 610-618;
D. Schröder, H. Schwarz, Angew. Chem. Int. Ed. Engl. 1995, 34, 1973-1995;
F. Song, T. Gou, B. Q. Wang, Z. J. Shi, Chem. Soc. Rev. 2018, 47, 7078-7115;
P. Sivaguru, Z. Wang, G. Zanoni, X. Bi, Chem. Soc. Rev. 2019, 48, 2615-2656;
L. Deng, G. Dong, Trends Chem. 2020, 2, 183-198.
G. Huang, L. Lu, H. Jiang, B. Yin, Chem. Commun. 2017, 53, 12217-12220;
G. Huang, B. Yin, Adv. Synth. Catal. 2019, 361, 5576-5586.
For C−C bond activation of alcoholates see
H. Harayama, T. Kuroki, M. Kimura, S. Tanaka, Y. Tamaru, Angew. Chem. Int. Ed. Engl. 1997, 36, 2352-2354;
H.-F. Chow, C.-W. Wan, K.-H. Low, Yeung, J. Org. Chem. 2001, 66, 1910-1913;
X. Dou, Y. Huang, T. Hayashi, Angew. Chem. Int. Ed. 2016, 55, 1133-1137;
Y. Terao, H. Wakui, T. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc. 2001, 123, 10407-10408;
Y. Terao, H. Wakui, M. Nomoto, T. Satoh, M. Miura, M. Nomura, J. Org. Chem. 2003, 68, 5236-5243;
J.-A. Ahn, D.-H. Chang, Y. J. Park, Y. R. Yon, A. Loupy, C.-H. Jun, Adv. Synth. Catal. 2006, 348, 55-58.
For decarbonylative coupling see:
L. Guo, M. Rueping, Acc. Chem. Res. 2018, 51, 1185-1195;
L. Guo, M. Rueping, Chem. Eur. J. 2018, 24, 7794-7809.
L. Guo, W. Srimontree, C. Zhu, B. Maity, X. Liu, L. Cavallo, M. Rueping, Nat. Commun. 2019, 10, 1957;
M. Kazemnejadi, R. O. Ahmed, B. Mahmoudi, RSC Adv. 2020, 10, 43962-43974.
For decarboxylative coupling see
N. Rodríguez, L. J. Goossen, Chem. Soc. Rev. 2011, 40, 5030;
L. J. Gooßen, N. Rodríguez, K. Gooßen, Angew. Chem. Int. Ed. 2008, 47, 3100-3120.
F. Chacón-Huete, J. D. Lasso, P. Szavay, J. Covone, P. Forgione, J. Org. Chem. 2021, 86, 515-524;
P. Forgione, M. Brochu, M. St-Onge, K. H. Thesen, M. D. Bailey, F. Bilodeau, J. Am. Chem. Soc. 2006, 128, 11350-11351;
F. Chacón-Huete, D. Mangel, M. Ali, A. Sudano, P. Forgione, ACS Sustainable Chem. Eng. 2017, 5, 7071-7076;
F. Chacón-Huete, J. Covone, L. Zaroubi, P. Forgione, Eur. J. Org. Chem. 2022, 8, e202101571.
J. M. Wood, D. P. Furkert, M. A. Brimble, Org. Biomol. Chem. 2016,14, 7659-7664.
F. Tellier, R. Sauvêtre, J−F. Normant, J. Organomet. Chem. 1985, 292, 19-28.
R. Galaverna, M. C. Breitkreitz, J. C. Pastre, ACS Sustainable Chem. Eng. 2018, 6, 4220-4230.
K. S. Kozlov, L. V. Romashov, V. P. Ananikov, Green Chem. 2019, 21, 3464-3468.
H. Ishikawa, M. Sheng, A. Nakata, K. Nakajima, S. Yamazoe, J. Yamasaki, S. Yamaguchi, T. Mizugaki, T. Mitsudome, ACS Catal. 2021, 11, 750-757.
F. Chacón-Huete, J. Covone, L. Zaroubi, P. Forgione, Eur. J. Org. Chem. 2022, e202101.
G. G. Xu, P. P. Pagare, M. S. Ghatge, R. P. Safo, A. Gazi, Q. Chen, T. David, A. B. Alabbas, F. N. Musayev, J. Venitz, Y. Zhang, M. K. Safo, O. Abdulmalik, Mol. Pharmaceutics 2017, 14(10), 3499-3511.
P.-F. Koh, T.-P. Loh, Green Chem. 2015, 17, 3746-3750.
M. Maity, U. Maitra, J. Mater. Chem. A 2014, 2, 18952-18958.
S. Rajendran, R. Raghunathan, I. Hevus, R. Krishnan, A. Ugrinov, M. P. Sibi, D. C. Webster, J. Sivaguru, Angew. Chem. Int. Ed. 2015, 54, 1159-1163.
F. Chacón-Huete, C. Messina, F. Chen, L. Cuccia, X. Ottaenwalder, P. Forgione, Green Chem. 2018, 20, 5261-5265.
T. N. Hooper, R. K. Brown, F. Rekhroukh, M. Garçon, A. J. P. Whitea, P. J. Costa, M. R. Crimmin, Chem. Sci. 2020,11, 7850-7857.
F. Witte, S. P. Zucker, B. Paulus, C. C. Tzschucke, Organometallics 2021, 40, 591-599;
V. De Felice, A. de Renzi, N. Fraldi, B. Panunzi, Inorg. Chim. Acta 2009, 362, 2015-2019.
K. O. Marichev, Y. Wang, A. M. Carranco, E. C. Garcia, Z.-X. Yu, M. P. Doyle, Chem. Commun. 2018, 54, 9513-9516.
H. Sheng, Q. Liu, B.-B. Zhang, Z.-X. Wang, X.-Y. Chen, Angew. Chem. Int. Ed. 2023, 62, e202218468.
E. G. Babcock, Md. S. Rahman, J. E. Taylor, Org. Biomol. Chem. 2023, 21, 163-168.