Tuning the Regioselective Functionalization of Trifluoromethylated Dienes via Lanthanum-Mediated Single C-F Bond Activation.
C−C coupling
C−F activation
fulvene
lanthanides
mechanism
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
24 Feb 2021
24 Feb 2021
Historique:
received:
07
12
2020
pubmed:
13
1
2021
medline:
13
1
2021
entrez:
12
1
2021
Statut:
ppublish
Résumé
The development of new fluorine-containing building blocks and their efficient synthetic access is currently a challenging research field. Herein, the highly regio- and stereoselective addition of a large range of aldehydes onto trifluoromethylated benzofulvenes was achieved using a simple La/I
Identifiants
pubmed: 33433035
doi: 10.1002/chem.202005239
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
4016-4021Subventions
Organisme : Agence Nationale de la Recherche
ID : ANR-15-CE29-0020-01
Organisme : Centre National de la Recherche Scientifique
Organisme : Chinese Government Scholarship
Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
J. Han, A. M. Remete, L. S. Dobson, L. Kiss, K. Izawa, H. Moriwaki, V. A. Soloshonok, D. O'Hagan, J. Fluorine Chem. 2020, 239, 109639;
J. Moschner, V. Stulberg, R. Fernandes, S. Huhmann, J. Leppkes, B. Koksch, Chem. Rev. 2019, 119, 10718-10801;
T. Fujiwara, D. O'Hagan, J. Fluorine Chem. 2014, 167, 16-29;
B. Ameduri, Chem. Eur. J. 2018, 24, 18830-18841;
Q. Fan, U. A. Méndez-Romero, X. Guo, E. Wang, M. Zhang, Y. Li, Chem. Asian J. 2019, 14, 3085-3095.
Selected reviews on fluorination methods:
F.-G. Zhang, X.-Q. Wang, Y. Zhou, H.-S. Shi, Z. Feng, J.-A. Ma, I. Marek, Chem. Eur. J. 2020, 26, 15378-15396;
T. Fuchigami, S. Inagi, Acc. Chem. Res. 2020, 53, 322-334;
R. Szpera, D. F. J. Moseley, L. B. Smith, A. J. Sterling, V. Gouverneur, Angew. Chem. Int. Ed. 2019, 58, 14824-14848;
Angew. Chem. 2019, 131, 14966-14991;
D. E. Yerien, S. Barata-Vallejo, A. Postigo, Chem. Eur. J. 2017, 23, 14676-14701;
M. G. Campbell, T. Ritter, Chem. Rev. 2015, 115, 612-633.
H. Amii, K. Uneyama, Chem. Rev. 2009, 109, 2119-2183;
T. Ahrens, T. Braun, Chem. Rev. 2015, 115, 931-972;
A. Arora, J. D. Weaver, Acc. Chem. Res. 2016, 49, 2273-2283;
Y. Wang, A. Liu, Chem. Soc. Rev. 2020, 49, 4906-4925.
F. Jaroschik, Chem. Eur. J. 2018, 24, 14572-14582;
J.-D. Hamel, J.-F. Paquin, Chem. Commun. 2018, 54, 10224-10239;
T. Fujita, K. Fuchibe, J. Ichikawa, Angew. Chem. Int. Ed. 2019, 58, 390-402;
Angew. Chem. 2019, 131, 396-408;
F. Tian, G. Yan, J. Yu, Chem. Commun. 2019, 55, 13486-13505;
R. Gupta, A. K. Jaiswal, D. Mandal, R. D. Young, Synlett 2020, 31, 933-937.
X.-T. Gao, Z. Zhang, X. Wang, J.-S. Tian, S.-L. Xie, F. Zhou, J. Zhou, Chem. Sci. 2020, 11, 10414-10420;
D. Ding, Y. Lan, Z. Lin, C. Wang, Org. Lett. 2019, 21, 2723-2730;
Y. Jin, J. Wu, Z. Lin, Y. Lan, C. Wang, Org. Lett. 2020, 22, 5347-5352;
Y. He, D. Anand, Z. Sun, L. Zhou, Org. Lett. 2019, 21, 3769-3773;
G. Chen, L. Wang, X. Liu, P. Liu, Adv. Synth. Catal. 2020, 362, 2990-2996;
Y. Liu, C. Li, C. Liu, J. He, X. Zhao, S. Cao, Tetrahedron Lett. 2020, 61, 151940;
S. B. Lang, R. J. Wiles, C. B. Kelly, G. A. Molander, Angew. Chem. Int. Ed. 2017, 56, 15073-15077;
Angew. Chem. 2017, 129, 15269-15273;
T. Ichitsuka, T. Fujita, J. Ichikawa, ACS Catal. 2015, 5, 5947-5950;
Y. Huang, T. Hayashi, J. Am. Chem. Soc. 2016, 138, 12340-12343;
K. Fuchibe, H. Hatta, K. Oh, R. Oki, J. Ichikawa, Angew. Chem. Int. Ed. 2017, 56, 5890-5893;
Angew. Chem. 2017, 129, 5984-5987;
T. Xiao, L. Li, L. Zhou, J. Org. Chem. 2016, 81, 7908-7916;
X. Lu, X.-X. Wang, T.-J. Gong, J.-J. Pi, S.-J. He, Y. Fu, Chem. Sci. 2019, 10, 809-814;
Y. Cai, H. Zeng, C. Zhu, C. Liu, G. Liu, H. Jiang, Org. Chem. Front. 2020, 7, 1260-1265;
R. J. Wiles, J. P. Phelan, G. A. Molander, Chem. Commun. 2019, 55, 7599-7602.
Direct ipso-substitution:
N. A. Phillips, G. J. Coates, A. J. P. White, M. R. Crimmin, Chem. Eur. J. 2020, 26, 5365-5368;
H. Zeng, C. Zhu, H. Jiang, Org. Lett. 2019, 21, 1130-1133;
S.-S. Yan, D.-S. Wu, J.-H. Ye, L. Gong, X. Zeng, C.-K. Ran, Y.-Y. Gui, J. Li, D.-G. Yu, ACS Catal. 2019, 9, 6987-6992.
Formal ipso-substitution via isolated boron-intermediate: R. Kojima, S. Akiyama, H. Ito, Angew. Chem. Int. Ed. 2018, 57, 7196-7199;
Angew. Chem. 2018, 130, 7314-7317;
P. H. S. Paioti, J. Del Pozo, M. S. Mikus, J. Lee, M. J. Koh, F. Romiti, S. Torker, A. H. Hoveyda, J. Am. Chem. Soc. 2019, 141, 19917-19934;
P. Gao, G. Wang, L. Xi, M. Wang, S. Li, Z. Shi, Chin. J. Chem. 2019, 37, 1009-1014;
P. Gao, C. Yuan, Y. Zhao, Z. Shi, Chem 2018, 4, 2201-2211;
Y. Liu, Y. Zhou, Y. Zhao, J. Qu, Org. Lett. 2017, 19, 946-949.
T. Nagai, M. Hama, M. Yoshioka, M. Yuda, N. Yoshida, A. Ando, M. Koyama, T. Miki, I. Kumadaki, Chem. Pharm. Bull. 1989, 37, 177-183.
H. Chen, D. Anand, L. Zhou, Asian J. Org. Chem. 2019, 8, 661-664.
T. Kumar, F. Massicot, D. Harakat, S. Chevreux, A. Martinez, K. Bordolinska, P. Preethanuj, R. Kokkuvayil Vasu, J.-B. Behr, J.-L. Vasse, F. Jaroschik, Chem. Eur. J. 2017, 23, 16460-16465.
T. Kumar, A. Ben Hassine, A. Martinez, D. Harakat, S. Chevreux, F. Massicot, M. Taillefer, J.-B. Behr, J.-L. Vasse, F. Jaroschik, J. Vis. Exp. 2018, 137, e57948.
Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293;
S. Wu, Y. Li, S. Zhang, J. Org. Chem. 2016, 81, 8070-8076;
X. Y. Cao, F. Huang, S. Zhang, Synlett 2019, 30, 1437-1441.
M. Fischer, K. Fitschen, M. Schmidtmann, R. Beckhaus, Organometallics 2019, 38, 3760-3767;
S. Tortorella, M. Mastropasqua Talamo, A. Cardone, M. Pastore, F. De Angelis, J. Phys. Condens. Matter 2016, 28, 074005;
A. Cappelli, V. Razzano, G. Fabio, M. Paolino, G. Grisci, G. Giuliani, A. Donati, R. Mendichi, W. Mróz, F. Villafiorita-Monteleone, C. Botta, RSC Adv. 2015, 5, 101377-101385.
G. Chelucci, Chem. Rev. 2012, 112, 1344-1462;
X. Zhang, S. Cao, Tetrahedron Lett. 2017, 58, 375-392.
J. Cheng, D. Cui, W. Chen, T. Tang, B. Huang, Polyhedron 2004, 23, 1075-1080;
Y. Wang, Y. Lei, S. Chi, Y. Luo, Dalton Trans. 2013, 42, 1862-1871;
C.-T. Qian, G. Zou, W.-L. Nie, J. Sun, D. A. Lemenovskii, M. V. Borzov, Polyhedron 2000, 19, 1955-1959.