Vinylic Trifluoromethylselenolation via Pd-Catalyzed C-H Activation.
C−H functionalization
fluorine
selenium
trifluoromethylselenolation
trifluoromethylselenosulfonate
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
11 Nov 2022
11 Nov 2022
Historique:
received:
22
07
2022
pubmed:
9
8
2022
medline:
9
8
2022
entrez:
8
8
2022
Statut:
ppublish
Résumé
Trifluorometylselenolation via C-H activation is barely described in literature. In particular, no such vinylic functionalization has been yet described. Herein, a palladium-catalyzed trifluoromethylselenolation of vinylic C-H bonds is described. The 5-methoxy-8-aminoquinoline has been used as auxiliary directing group to perform this reaction. The reaction gives excellent yields with α-substituted compounds whatever the substituents and a microwave activation can be used to accelerate the reaction. With β-substituted substrates lower yields, but still satisfactory, are obtained. This methodology was also successfully extended to other fluoroalkylselenyl groups.
Identifiants
pubmed: 35938688
doi: 10.1002/chem.202202299
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202202299Subventions
Organisme : Agence Nationale de la Recherche
ID : 18-CE07-0039-01
Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
B. E. Smart, J. Fluorine Chem. 2001, 109, 3-11;
P. Kirsch, Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2013;
R. Mondal, M. Agbaria, Z. Nairoukh, Chem. Eur. J. 2021, 27, 7193-7213.
Y. Zhou, J. Wang, Z. Gu, S. Wang, W. Zhu, J. L. Aceña, V. A. Soloshonok, K. Izawa, H. Liu, Chem. Rev. 2016, 116, 422-518;
N. A. Meanwell, J. Med. Chem. 2018, 61, 5822-5880;
H. Mei, J. Han, S. Fustero, M. Medio-Simon, D. M. Sedgwick, C. Santi, R. Ruzziconi, V. A. Soloshonok, Chem. Eur. J. 2019, 25, 11797-11819;
M. Inoue, Y. Sumii, N. Shibata, ACS Omega 2020, 5, 10633-10640;
A. Abula, Z. Xu, Z. Zhu, C. Peng, Z. Chen, W. Zhu, H. A. Aisa, J. Chem. Inf. Model. 2020, 60, 6242-6250;
B. M. Johnson, Y.-Z. Shu, X. Zhuo, N. A. Meanwell, J. Med. Chem. 2020, 63, 6315-6386;
M. Cheng, C. Guo, M. L. Gross, Angew. Chem. Int. Ed. 2020, 59, 5880-5889;
Angew. Chem. 2020, 132, 5932-5942;
H. Mei, J. Han, S. White, D. J. Graham, K. Izawa, T. Sato, S. Fustero, N. A. Meanwell, V. A. Soloshonok, Chem. Eur. J. 2020, 26, 11349-11390;
C. Zhang, K. Yan, C. Fu, H. Peng, C. J. Hawker, A. K. Whittaker, Chem. Rev. 2022, 122, 167-208;
D. Janasik, T. Krawczyk, Chem. Eur. J. 2022, 28, e202102556;
P. Jeschke, Pest Manage. Sci. 2010, 66, 10-27;
T. Fujiwara, D. O'Hagan, J. Fluorine Chem. 2014, 167, 16-29;
Y. Ogawa, E. Tokunaga, O. Kobayashi, K. Hirai, N. Shibata, iScience 2020, 23, 101467;
P. Jeschke, Eur. J. Org. Chem. 2022, 2022, e202101513;
R. Berger, G. Resnati, P. Metrangolo, E. Weber, J. Hulliger, Chem. Soc. Rev. 2011, 40, 3496-3508;
M. Pagliaro, R. Ciriminna, J. Mater. Chem. 2005, 15, 4981-4991;
D. Chopra, T. N. G. Row, CrystEngComm 2011, 13, 2175-2186;
Fascinating Fluoropolymers and Their Applications (Eds: B. Ameduri, S. Fomin), Elsevier, Amsterdam, Netherlands, 2020;
J. Lv, Y. Cheng, Chem. Soc. Rev. 2021, 50, 5435-5467;
B. Améduri, Macromol. Chem. Phys. 2020, 221, 1900573;
S. Dolui, D. Kumar, S. Banerjee, B. Ameduri, Acc. Mater. Res. 2021, 2, 242-251.
Emerging Fluorinated Motifs: Synthesis, Properties and Applications (Eds: D. Cahard, J. A. Ma), Wiley, Weinheim, Germany, 2020.
A. Leo, C. Hansch, D. Elkins, Chem. Rev. 1971, 71, 525-616;
C. Hansch, A. Leo, S. H. Unger, K. H. Kim, D. Nikaitani, E. J. Lien, J. Med. Chem. 1973, 16, 1207-1216;
K. Grollier, A. De Zordo-Banliat, F. Bourdreux, B. Pegot, G. Dagousset, E. Magnier, T. Billard, Chem. Eur. J. 2021, 27, 6028-6033.
B. Fan, F. Lin, X. Wu, Z. Zhu, A. K. Y. Jen, Acc. Chem. Res. 2021, 54, 3906-3916;
H. Chuai, S.-Q. Zhang, H. Bai, J. Li, Y. Wang, J. Sun, E. Wen, J. Zhang, M. Xin, Eur. J. Med. Chem. 2021, 223, 113621;
Q. Li, Y. Zhang, Z. Chen, X. Pan, Z. Zhang, J. Zhu, X. Zhu, Org. Chem. Front. 2020, 7, 2815-2841;
W. Guo, Y. Fu, Chem. Eur. J. 2020, 26, 13322-13331;
Z. Chen, H. Lai, L. Hou, T. Chen, Chem. Commun. 2020, 56, 179-196;
G. C. Hoover, D. S. Seferos, Chem. Sci. 2019, 10, 9182-9188;
S. P. Short, J. M. Pilat, C. S. Williams, Free Radical Biol. Med. 2018, 127, 26-35;
Organoselenium Compounds in Biology and Medicine: Synthesis, Biological and Therapeutic Treatments (Eds: V. K. Jain, K. I. Priyadarsini), Royal Society of Chemistry, Croydon, UK, 2018;
V. Gandin, P. Khalkar, J. Braude, A. P. Fernandes, Free Radical Biol. Med. 2018, 127, 80-97;
J. B. T. Rocha, B. C. Piccoli, C. S. Oliveira, Arkivoc 2017, 457-491;
R. Mousa, R. Notis Dardashti, N. Metanis, Angew. Chem. Int. Ed. 2017, 56, 15818-15827;
Angew. Chem. 2017, 129, 16027-16037;
N. Singh, A. C. Halliday, J. M. Thomas, O. V. Kuznetsova, R. Baldwin, E. C. Y. Woon, P. K. Aley, I. Antoniadou, T. Sharp, S. R. Vasudevan, G. C. Churchill, Nat. Commun. 2013, 4, 1332;
K. M. Brown, J. R. Arthur, Public Health Nutr. 2001, 4, 593-599;
M. P. Rayman, Lancet 2000, 356, 233-241.
X. He, Y. Nie, M. Zhong, S. Li, X. Li, Y. Guo, Z. Liu, Y. Gao, F. Ding, D. Wen, Y. Zhang, Eur. J. Med. Chem. 2021, 218, 113384;
Z.-Z. Han, T. Dong, X.-X. Ming, F. Kuang, C.-P. Zhang, ChemMedChem 2021, 16, 3177-3180;
X. He, M. Zhong, S. Li, X. Li, Y. Li, Z. Li, Y. Gao, F. Ding, D. Wen, Y. Lei, Y. Zhang, Eur. J. Med. Chem. 2020, 208, 112864.
F. Toulgoat, F. Liger, T. Billard, in Organofluorine Chemistry: Synthesis, Modeling, and Applications (Eds: K. Szabó, N. Selander), Wiley-VCH, Weinheim, Germany, 2021, pp. 49-97;
X.-H. Yang, D. Chang, R. Zhao, L. Shi, Asian J. Org. Chem. 2021, 10, 61-73;
Y. Wang, Z. Ye, H. Zhang, Z. Yuan, Adv. Synth. Catal. 2021, 363, 1835-1854;
H.-N. Wang, J.-Y. Dong, J. Shi, C.-P. Zhang, Tetrahedron 2021, 99, 132476;
Y. Cao, N.-Y. Xu, A. Issakhov, A. G. Ebadi, M. R. Poor Heravi, E. Vessally, J. Fluorine Chem. 2021, 252, 109901.
C. Hou, X. Lin, Y. Huang, Z. Chen, Z. Weng, Synthesis 2015, 47, 969-975;
C. Wu, Y. Huang, Z. Chen, Z. Weng, Tetrahedron Lett. 2015, 56, 3838-3841;
P. Zhu, X. He, X. Chen, Y. You, Y. Yuan, Z. Weng, Tetrahedron 2014, 70, 672-677;
Y. Zhang, D.-Y. Yang, Z. Weng, Tetrahedron 2017, 73, 3853-3859.
S. R. Mudshinge, Y. Yang, B. Xu, G. B. Hammond, Z. Lu, Angew. Chem. Int. Ed. 2022, 61, e202115687.
Q. Lefebvre, R. Pluta, M. Rueping, Chem. Commun. 2015, 51, 4394-4397.
Q. Glenadel, C. Ghiazza, A. Tlili, T. Billard, Adv. Synth. Catal. 2017, 359, 3414-3420.
C. Ghiazza, L. Khrouz, C. Monnereau, T. Billard, A. Tlili, Chem. Commun. 2018, 54, 9909-9912;
C. Ghiazza, V. Debrauwer, T. Billard, A. Tlili, Chem. Eur. J. 2018, 24, 97-100;
B.-S. Zhang, L.-Y. Gao, Z. Zhang, Y.-H. Wen, Y.-M. Liang, Chem. Commun. 2018, 54, 1185-1188;
C. Ghiazza, A. Tlili, T. Billard, Beilstein J. Org. Chem. 2017, 13, 2626-2630.
K. Grollier, A. Taponard, C. Ghiazza, E. Magnier, T. Billard, Helv. Chim. Acta 2020, 103, e2000185.
T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147-1169;
L. Ackermann, Chem. Rev. 2011, 111, 1315-1345;
J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. Int. Ed. 2012, 51, 8960-9009;
Angew. Chem. 2012, 124, 9092-9142;
C−H Bond Activation and Catalytic Functionalization II (Eds: P. H. Dixneuf, H. Doucet), Springer International Publishing, Switzerland, 2016;
Strategies for Palladium-Catalyzed Non-Directed and Directed C−H Bond Functionalization (Eds: A. R. Kapdi, D. Maiti), Elsevier, Amsterdam, Netherlands, 2017;
R. Sharma, U. Sharma, Catal. Rev. Sci. Eng. 2018, 60, 497-565;
T. Rogge, N. Kaplaneris, N. Chatani, J. Kim, S. Chang, B. Punji, L. L. Schafer, D. G. Musaev, J. Wencel-Delord, C. A. Roberts, R. Sarpong, Z. E. Wilson, M. A. Brimble, M. J. Johansson, L. Ackermann, Nat. Rev. Methods Primers 2021, 1, 43;
Remote C−H Bond Functionalizations: Methods and Strategies in Organic Synthesis (Eds: D. Maiti, S. Guin), WILEY-VCH, Weinheim, Germany, 2021.
C. Ghiazza, T. Billard, Eur. J. Org. Chem. 2021, 5571-5584.
K. Grollier, E. Chefdeville, E. Jeanneau, T. Billard, Chem. Eur. J. 2021, 27, 12910-12916.
Q. Zhao, T. Poisson, X. Pannecoucke, J.-P. Bouillon, T. Besset, Org. Lett. 2017, 19, 5106-5109.