Reusable Pd@PEG Catalyst for Aerobic Dehydrogenative C-H/C-H Arylations of 1,2,3-Triazoles.
C−H activation
arylation
oxidation
palladium
polyethylene glycol
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
02 Sep 2019
02 Sep 2019
Historique:
received:
25
06
2019
revised:
11
07
2019
pubmed:
16
7
2019
medline:
16
7
2019
entrez:
16
7
2019
Statut:
ppublish
Résumé
Dehydrogenative C-H arylations of 1,2,3-triazoles were accomplished with the aid of a reusable palladium catalyst in PEG. The widely applicable oxidative palladium catalysis enabled the synthesis of fully decorated 1,2,3-triazoles with a broad functional-group tolerance and ample substrate scope. The sustainability of the aerobic C-H arylation was reflected by the use of PEG as green reaction medium and demonstrated by recycling studies of the catalyst and the reaction medium.
Identifiants
pubmed: 31306515
doi: 10.1002/chem.201902901
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
11427-11431Subventions
Organisme : California Department of Fish and Game
ID : Gottfried-Wilhelm-Leibniz award
Organisme : Horizon 2020 Framework Programme
ID : 720996
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
S. Lin, A. Sharma, Chem. Heterocycl. Compd. 2018, 54, 314-316;
J. Huo, H. Hu, M. Zhang, X. Hu, M. Chen, D. Chen, J. Liu, G. Xiao, Y. Wang, Z. Wen, RSC Adv. 2017, 7, 2281-2287;
A. Marrocchi, A. Facchetti, D. Lanari, S. Santoro, L. Vaccaro, Chem. Sci. 2016, 7, 6298-6308.
M. Virelli, E. Moroni, G. Colombo, L. Fiengo, A. Porta, L. Ackermann, G. Zanoni, Chem. Eur. J. 2018, 24, 16516-16520;
B. K. Çavuşoğlu, L. Yurttaş, Z. Cantürk, Eur. J. Med. Chem. 2018, 144, 255-261;
B. Wang, B. Zhao, Z.-S. Chen, L.-P. Pang, Y.-D. Zhao, Q. Guo, X.-H. Zhang, Y. Liu, G.-Y. Liu, Z. Hao, X.-Y. Zhang, L.-Y. Ma, H.-M. Liu, Eur. J. Med. Chem. 2018, 143, 1535-1542;
T.-j. Zhang, S.-y. Li, Y. Zhang, Q.-x. Wu, F.-h. Meng, Chem. Biol. Drug Des. 2018, 91, 526-533;
Y. Zhang, G. L. V. Damu, S.-F. Cui, J.-L. Mi, V. K. R. Tangadanchu, C.-H. Zhou, MedChemComm 2017, 8, 1631-1639.
P. Gandeepan, L. Ackermann, Chem. 2018, 4, 199-222;
J. He, M. Wasa, K. S. L. Chan, Q. Shao, J.-Q. Yu, Chem. Rev. 2017, 117, 8754-8786;
D. L. Davies, S. A. Macgregor, C. L. McMullin, Chem. Rev. 2017, 117, 8649-8709;
Y. Park, Y. Kim, S. Chang, Chem. Rev. 2017, 117, 9247-9301;
Y. Wei, P. Hu, M. Zhang, W. Su, Chem. Rev. 2017, 117, 8864-8907.
D. Wang, A. B. Weinstein, P. B. White, S. S. Stahl, Chem. Rev. 2018, 118, 2636-2679;
A. M. Prendergast, Z. Zhang, Z. Lin, G. P. McGlacken, Dalton Trans. 2018, 47, 6049-6053;
K. Fukuzumi, Y. Nishii, M. Miura, Angew. Chem. Int. Ed. 2017, 56, 12746-12750;
Angew. Chem. 2017, 129, 12920-12924;
F. Ferlin, S. Santoro, L. Ackermann, L. Vaccaro, Green Chem. 2017, 19, 2510-2514;
X. Tian, F. Yang, D. Rasina, M. Bauer, S. Warratz, F. Ferlin, L. Vaccaro, L. Ackermann, Chem. Commun. 2016, 52, 9777-9780;
L. Ackermann, R. Jeyachandran, H. K. Potukuchi, P. Novák, L. Büttner, Org. Lett. 2010, 12, 2056-2059.
A. Bechtoldt, M. E. Baumert, L. Vaccaro, L. Ackermann, Green Chem. 2018, 20, 398-402;
S. Dana, D. Chowdhury, A. Mandal, F. A. S. Chipem, M. Baidya, ACS Catal. 2018, 8, 10173-10179;
S. Y. de Boer, T. J. Korstanje, S. R. La Rooij, R. Kox, J. N. H. Reek, J. I. van der Vlugt, Organometallics 2017, 36, 1541-1549; see also:
L. Ackermann, R. Born, R. Vicente, ChemSusChem 2009, 2, 546-549.
A. Lee, R. C. Betori, E. A. Crane, K. A. Scheidt, J. Am. Chem. Soc. 2018, 140, 6212-6216;
A. A. Almasalma, E. Mejía, Chem. Eur. J. 2018, 24, 12269-12273;
X. Wang, N. Li, Z. Li, H. Rao, J. Org. Chem. 2017, 82, 10158-10166;
X. Ji, D. Li, X. Zhou, H. Huang, G.-J. Deng, Green Chem. 2017, 19, 619-622.
S. Santoro, S. I. Kozhushkov, L. Ackermann, L. Vaccaro, Green Chem. 2016, 18, 3471-3493.
J. P. Hallett, T. Welton, Chem. Rev. 2011, 111, 3508-3576;
M. Cai, Y. Wang, W. Hao, Green Chem. 2007, 9, 1180-1184;
W. Miao, T. H. Chan, Org. Lett. 2003, 5, 5003-5005;
J. D. Revell, A. Ganesan, Org. Lett. 2002, 4, 3071-3073;
C. J. Mathews, P. J. Smith, T. Welton, Chem. Commun. 2000, 1249-1250.
J. Xia, M. Cheng, Q. Chen, M. Cai, Appl. Organomet. Chem. 2015, 29, 113-116;
H. Zhao, M. Cheng, J. Zhang, M. Cai, Green Chem. 2014, 16, 2515-2522;
Q. Zhou, S. Wei, W. Han, J. Org. Chem. 2014, 79, 1454-1460;
L. Ackermann, R. Vicente, Org. Lett. 2009, 11, 4922-4925;
W.-J. Zhou, K.-H. Wang, J.-X. Wang, J. Org. Chem. 2009, 74, 5599-5602;
W. Han, C. Liu, Z.-L. Jin, Org. Lett. 2007, 9, 4005-4007;
S. Shi, Y. Zhang, J. Org. Chem. 2007, 72, 5927-5930;
L. Wang, Y. Zhang, L. Liu, Y. Wang, J. Org. Chem. 2006, 71, 1284-1287;
J.-H. Li, W.-J. Liu, Y.-X. Xie, J. Org. Chem. 2005, 70, 5409-5412;
L. Liu, Y. Zhang, Y. Wang, J. Org. Chem. 2005, 70, 6122-6125;
S. Chandrasekhar, C. Narsihmulu, S. S. Sultana, N. R. Reddy, Org. Lett. 2002, 4, 4399-4401.
P. Migowski, K. L. Luska, W. Leitner, in Nanocatalysis in Ionic Liquids (Ed.: M. H. G. Prechtl), Wiley-VCH, Weinheim, 2016;
H.-P. Steinrück, P. Wasserscheid, Catal. Lett. 2015, 145, 380-397.
S.-K. Ruokonen, C. Sanwald, M. Sundvik, S. Polnick, K. Vyavaharkar, F. Duša, A. J. Holding, A. W. T. King, I. Kilpeläinen, M. Lämmerhofer, P. Panula, S. K. Wiedmer, Environ. Sci. Technol. 2016, 50, 7116-7125;
M. Kumar, N. Trivedi, C. R. K. Reddy, B. Jha, Chem. Res. Toxicol. 2011, 24, 1882-1890;
C. Chiappe, C. S. Pomelli, in Analytical Applications of Ionic Liquids (Ed.: M. Koehl), World Scientific, New Jersey, 2016, pp. 385-404.
D. Cespi, E. S. Beach, T. E. Swarr, F. Passarini, I. Vassura, P. J. Dunn, P. T. Anastas, Green Chem. 2015, 17, 3390-3400;
C. Jimenez-Gonzalez, C. S. Ponder, Q. B. Broxterman, J. B. Manley, Org. Process Res. Dev. 2011, 15, 912-917.
Alternative Energy Sources for Green Chemistry (Eds.: G. Stefanidis, A. Stankiewicz), The Royal Society of Chemistry, London, 2016, pp. 1-33;
Methods and Reagents for Green Chemistry: An Introduction (Eds.: A. Perosa, F. Zecchini), Wiley-VCH, Weinheim, 2007.
G. Parthasarathy, N. Kaplaneris, S. Santoro, L. Vaccaro, L. Ackermann, ACS Sustainable Chem. Eng. 2019, 7, 8023-8040.
V. Declerck, E. Colacino, X. Bantreil, J. Martinez, F. Lamaty, Chem. Commun. 2012, 48, 11778-11780;
N. R. Candeias, L. C. Branco, P. M. P. Gois, C. A. M. Afonso, A. F. Trindade, Chem. Rev. 2009, 109, 2703-2802;
D. E. Bergbreiter, J. Tian, C. Hongfa, Chem. Rev. 2009, 109, 530-582;
Z. A. Carlos Kleber, M. A. Luana, Curr. Org. Chem. 2005, 9, 195-218;
J. Chen, S. K. Spear, J. G. Huddleston, R. D. Rogers, Green Chem. 2005, 7, 64-82.
P. Gandeepan, T. Müller, D. Zell, G. Cera, S. Warratz, L. Ackermann, Chem. Rev. 2019, 119, 2192-2452;
S. Santoro, F. Ferlin, L. Luciani, L. Ackermann, L. Vaccaro, Green Chem. 2017, 19, 1601-1612;
M. Moselage, J. Li, L. Ackermann, ACS Catal. 2016, 6, 498-525;
W. Liu, L. Ackermann, ACS Catal. 2016, 6, 3743-3752;
S. De Sarkar, W. Liu, S. I. Kozhushkov, L. Ackermann, Adv. Synth. Catal. 2014, 356, 1461-1479;
L. Ackermann, Acc. Chem. Res. 2014, 47, 281-295;
L. Ackermann, J. Org. Chem. 2014, 79, 8948-8954;
L. Ackermann, Chem. Rev. 2011, 111, 1315.
T. Hosokawa, T. Uno, S. Inui, S. Murahashi, J. Am. Chem. Soc. 1981, 103, 2318-2323.