Unimolecular Reactivity of [Cu(R)(CF

copper cross coupling mass spectrometry quantum chemical calculations reaction mechanisms trifluoromethylation

Journal

Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783

Informations de publication

Date de publication:
20 Jul 2023
Historique:
received: 06 03 2023
medline: 4 5 2023
pubmed: 4 5 2023
entrez: 4 5 2023
Statut: ppublish

Résumé

The cuprate complexes [Cu(R)(CF

Identifiants

pubmed: 37139922
doi: 10.1002/chem.202300725
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

e202300725

Subventions

Organisme : Deutsche Forschungsgemeinschaft
ID : KO2875/12-1
Organisme : Deutsche Forschungsgemeinschaft
ID : INST 186/1326-1 FUGG
Organisme : Niedersächsische Ministerium für Wissenschaft und Kultur

Informations de copyright

© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Références

P. Shah, A. D. Westwell, J. Enzyme Inhib. Med. Chem. 2007, 22, 527-540.
 
K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881-1886;
W. K. Hagmann, J. Med. Chem. 2008, 51, 4359-4369;
J. Wang, M. Sánchez-Roselló, J. L. Aceña, C. Del Pozo, A. E. Sorochinsky, S. Fustero, V. A. Soloshonok, H. Liu, Chem. Rev. 2014, 114, 2432-2506; d)
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.
 
T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470-477;
T. Besset, T. Poisson, X. Pannecoucke, Eur. J. Org. Chem. 2015, 2015(13), 2765-2789;
C. Alonso, E. Martínez de Marigorta, G. Rubiales, F. Palacios, Chem. Rev. 2015, 115, 1847-1935; d)
P. Gao, X.-R. Song, X.-Y. Liu, Y.-M. Liang, Chem. Eur. J. 2015, 21, 7648-7661.
 
G. G. Dubinina, J. Ogikubo, D. A. Vicic, Organometallics 2008, 27, 6233-6235;
G. G. Dubinina, H. Furutachi, D. A. Vicic, J. Am. Chem. Soc. 2008, 130, 8600-8601;
O. A. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475-4521; d)
O. A. Tomashenko, E. C. Escudero-Adán, M. M. Belmonte, V. V. Grushin, Angew. Chem. Int. Ed. 2011, 50, 7655-7659;
Angew. Chem. 2011, 123, 7797-7801; e)
H. Morimoto, T. Tsubogo, N. D. Litvinas, J. F. Hartwig, Angew. Chem. Int. Ed. 2011, 50, 3793-3798;
Angew. Chem. 2011, 123, 3877-3882.
D. Naumann, T. Roy, K.-F. Tebbe, W. Crump, Angew. Chem. Int. Ed. 1993, 32, 1482-1483;
Angew. Chem. 1993, 105, 1555-1556.
A. M. Romine, N. Nebra, A. I. Konovalov, E. Martin, J. Benet-Buchholz, V. V. Grushin, Angew. Chem. Int. Ed. 2015, 54, 2745-2749;
Angew. Chem. 2015, 127, 2783-2787.
 
J. P. Snyder, Angew. Chem. Int. Ed. 1995, 34, 80-81;
Angew. Chem. 1995, 107, 112-113;
R. C. Walroth, J. T. Lukens, S. N. MacMillan, K. D. Finkelstein, K. M. Lancaster, J. Am. Chem. Soc. 2016, 138, 1922-1931;
C. Gao, G. Macetti, J. Overgaard, Inorg. Chem. 2019, 58, 2133-2139; d)
I. F. Leach, R. W. A. Havenith, J. E. M. N. Klein, Eur. J. Inorg. Chem. 2022, e202200247.
S.-L. Zhang, C. Xiao, H.-X. Wan, Dalton Trans. 2018, 47, 4779-4784.
M. Paeth, S. B. Tyndall, L.-Y. Chen, J.-C. Hong, W. P. Carson, X. Liu, X. Sun, J. Liu, K. Yang, E. M. Hale, D. L. Tierney, B. Liu, Z. Cao, M.-J. Cheng, W. A. Goddard III, W. Liu, J. Am. Chem. Soc. 2019, 141, 3153-3159.
Z. Lu, H. Liu, S. Liu, X. Leng, Y. Lan, Q. Shen, Angew. Chem. Int. Ed. 2019, 58, 8510-8514;
Angew. Chem. 2019, 131, 8598-8602.
For earlier reports on copper-mediated trifluormethylation reactions using boronic acids without the isolation of [Cu(R)(CF3)3]−, see:
L. Chu, F.-L. Qing, Org. Lett. 2010, 12, 5060-5063;
X. Jiang, L. Chu, F.-L. Qing, J. Org. Chem. 2012, 77, 1251-1257;
S.-L. Zhang, W.-F. Bie, RSC Adv. 2016, 6, 70902-70906.
 
H. Schwarz, Chem. i. uns. Zeit 1991, 25, 268-278;
R. A. J. O'Hair, Chem. Commun. 2006, 1469-1481;
K. L. Vikse, J. S. McIndoe, Pure Appl. Chem. 2015, 87, 361-377.
 
A. Putau, H. Brand, K. Koszinowski J. Am. Chem. Soc. 2012, 134, 613-622;
S. Weske, R. Schoop, K. Koszinowski, Chem. Eur. J. 2016, 22, 1-8;
T. Auth, C. J. Stein, R. A. J. O'Hair, K. Koszinowski, Chem. Eur. J. 2022, 28, e202103130.
M. Baya, D. Joven-Sancho, P. J. Alonso, J. Orduna, B. Menjón, Angew. Chem. Int. Ed. 2019, 58, 9954-9958;
Angew. Chem. 2019, 131, 10059-10063.
Note that the present experiments cannot distinguish cis/trans isomers.
H. Shen, Z. Liu, P. Zhang, X. Tan, Z. Zhang, C. Li, J. Am. Chem. Soc. 2017, 139, 9843-9846.
For a recent report of the preparation of [(bpy)Cu(C6F5)(CF3)2] and related complexes, see: G. Wang, M. Li, X. Leng, X. Xue, Q. Shen, Chin. J. Chem. 2022, 40, 1924-1930.
J. Hioe, H. Zipse in Encyclopedia of Radicals in Chemistry, Biology and Materials, Wiley, 2012, pp. 449-476.
For the heteroleptic complexes, the stepwise expulsion of R⋅ and CF3⋅ radicals obviously differs from the loss of two CF3⋅ radicals from the homoleptic complex; thus rendering a direct comparison between the different reactions more difficult. However, the fact that the heteroleptic complexes preferentially expel an R⋅ and a CF3⋅ radical instead of two CF3⋅ radicals suggests that the former reaction channel is energetically even more favorable than the latter. Thus, the [Cu(CF3)2]− fragment ions formed by the stepwise loss of an R⋅ and a CF3⋅ radical will not contain sufficient energy to undergo a consecutive CF2 elimination either.
J. Shearer, D. Vasiliauskas, K. M. Lancaster, Chem. Commun. 2023, 59, 98-101.
Q. Zhang, Y. Lium, T. Wang, X. Zhang, C. Long, Y.-D. Wu, M.-X. Wang, J. Am. Chem. Soc. 2018, 140, 5579-5587.
R. Hoffmann, S. Alvarez, C. Mealli, A. Falceto, T. J. Cahill III, T. Zeng, G. Manca, Chem. Rev. 2016, 116, 8173-8192.
C. W. Bauschlicher Jr, S. R. Langhoff, H. Partridge, J. Chem. Phys. 1991, 94, 2068-2072.
Y.-R. Luo, Handbook of Bond Dissociation Energies in Organic Compounds, CRC Press, 2002, Boca Raton.
U. Tasić, P. Hein, D. Troya, J. Phys. Chem. A 2007, 111, 3618-3632.
M. Deuker, Y. Yang, R. A. J. O′Hair, K. Koszinowski, Organometallics 2021, 40, 2354-2363.
S. Liu, H. Liu, S. Liu, Z. Lu, C. Lu, X. Leng, Y. Lan, Q. Shen, J. Am. Chem. Soc. 2020, 142, 9785-8791.
K. L. Vikse, M. P. Woods, J. S. McIndoe, Organometallics 2010, 29, 6615-6618.
 
F. Neese, Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2012, 2, 73-78;
F. Neese, Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2018, 8, e1327;
ORCA, version 4.2.1, Max Planck Institute for Chemical Energy Conversion, Mülheim a. d. Ruhr (Germany), 2019;
F. Neese, F. Wennmohs, U. Becker, C. Riplinger, J. Chem. Phys. 2020, 152, 224108.
C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158-6170.
 
S. Grimme, J. Antony, S. Ehrlich and H. Krieg, J. Chem. Phys. 2010, 132, 154104;
S. Grimme, S. Ehrlich, L. Goerigk, J. Comput. Chem. 2011, 32, 1456-1465.
F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
M. Dolg, U. Wedig, H. Stoll, H. Preuss, J. Chem. Phys. 1987, 86, 866-872.
 
C. Riplinger, F. Neese, J. Chem. Phys. 2013, 138, 034106;
C. Riplinger, B. Sandhoefer, A. Hansen, F. Neese, J. Chem. Phys. 2013, 139, 134101;
C. Riplinger, P. Pinski, U. Becker, E. F. Valeev, F. Neese, J. Chem. Phys. 2016, 144, 024109; d)
M. Saitow, U. Becker, C. Riplinger, E. F. Valeev, F. Neese, J. Chem. Phys. 2017, 146, 164105; e)
Y. Guo, C. Riplinger, U. Becker, D. G. Liakos, Y. Minenkov, L. Cavallo, F. Neese, J. Chem. Phys. 2018, 148, 011101; f)
Y. Guo, C. Riplinger, D. G. Liakos, U. Becker, M. Saitow, F. Neese, J. Chem. Phys. 2020, 152, 024116.
T. H. Dunning, Jr, J. Chem. Phys. 1989, 90, 1007-1023.
F. Weigend, A. Köhn, C. Hättig, J. Chem. Phys. 2002, 116, 3175-3183.
D. Figgen, G. Rauhut, M. Dolg, H. Stoll, Chem. Phys. 2005, 311, 227-244.
K. A. Peterson, C. Puzzarini, Theor. Chem. Acc. 2005, 114, 283-296.
S. Grimme, Chem. Eur. J. 2012,18, 9955-9964.
S. J. Klippenstein, A. F. Wagner, S. H. Robertson, R. C. Dunbar, D. M. Wardlaw, VariFlex, version 1.0, Argonne National Laboratory, Lemont (IL), 1999.
J. Troe, V. G. Ushakov, A. A. Viggiano, J. Phys. Chem. A 2006, 110, 1491-1499.

Auteurs

Bastian Zimmer (B)

Institut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstr. 2, 37077, Göttingen, Germany.

Thomas Auth (T)

Institut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstr. 2, 37077, Göttingen, Germany.

Konrad Koszinowski (K)

Institut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstr. 2, 37077, Göttingen, Germany.
Wöhler Research Institute for Sustainable Chemistry, Universität Göttingen, Tammannstr. 2, 37077, Göttingen, Germany.

Classifications MeSH