Recent Advances in Monofluorinated Carbenes, Carbenoids, Ylides, and Related Species.
carbenes
carbenoids
fluorine
monofluorocarbene
ylides
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 Dec 2023
11 Dec 2023
Historique:
received:
15
06
2023
medline:
30
10
2023
pubmed:
30
10
2023
entrez:
30
10
2023
Statut:
ppublish
Résumé
The synthesis of monofluorinated compounds is of great interest because of the vast applications of organofluorine compounds. Recently, the introduction of monofluorocarbene synthons has emerged as an important strategy for the synthesis of fluorine-containing products. In contrast to direct fluorination, in which C-F bonds are formed, the use of monofluorinated carbenes and related reactive species involves C-C or C-X bond formation while delivering valuable fluorine atoms into the target structure. Owing to increased knowledge on carbon-carbon and carbon-heteroatom bond formations, monofluorinated carbenes have enormous potential for the synthesis of organofluorine compounds, which, in our opinion, has not yet been fully exploited. This review summarizes the recent advances in the synthetic applications of monofluorinated carbenes, carbenoids, ylides, and related species.
Identifiants
pubmed: 37902650
doi: 10.1002/chem.202301851
doi:
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202301851Subventions
Organisme : Latvijas Zinātnes Padome
ID : lzp-2022/1-0335
Organisme : European Social Fund
ID : 8.2.2.0/20/l/008
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
R. Berger, G. Resnati, P. Metrangolo, E. Weber, J. Hulliger, Chem. Soc. Rev. 2011, 40, 3496-3508.
A. F. Brooks, J. J. Topczewski, N. Ichiishi, M. S. Sanford, P. J. H. Scott, Chem. Sci. 2014, 5, 4545-4553;
I. Tirotta, V. Dichiarante, C. Pigliacelli, G. Cavallo, G. Terraneo, F. B. Bombelli, P. Metrangolo, G. Resnati, Chem. Rev. 2015, 115, 1106-1129;
C. Zhang, K. Yan, C. Fu, H. Peng, C. J. Hawker, A. K. Whittaker, Chem. Rev. 2022, 122, 167-208.
M. Cheng, C. Guo, M. L. Gross, Angew. Chem. Int. Ed. 2020, 59, 5880-5889;
H. Chen, S. Viel, F. Ziarelli, L. Peng, Chem. Soc. Rev. 2013, 42, 7971-7982.
E. P. Gillis, K. J. Eastman, M. D. Hill, D. J. Donnelly, N. A. Meanwell, J. Med. Chem. 2015, 58, 8315-8359;
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;
S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320-330;
H.-J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, M. Stahl, ChemBioChem 2004, 5, 637-643;
C. Isanbor, D. O'Hagan, J. Fluorine Chem. 2006, 127, 303-319.
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;
Q. Wang, H. Song, Q. Wang, Chin. Chem. Lett. 2022, 33, 626-642.
S.-F. Zhu, Q.-L. Zhou, Acc. Chem. Res. 2012, 45, 1365-1377;
D. Zhu, L. Chen, H. Fan, Q. Yao, S. Zhu, Chem. Soc. Rev. 2020, 49, 908-950;
H. M. L. Davies, D. Morton, Chem. Soc. Rev. 2011, 40, 1857-1869;
H. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861-2904;
B. Wang, D. Qiu, Y. Zhang, J. Wang, Beilstein J. Org. Chem. 2016, 12, 796-804;
M. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 2010, 110, 704-724;
X. Zhao, G. Wang, A. S. K. Hashmi, ChemCatChem 2021, 13, 4299-4312;
H. Keipour, V. Carreras, T. Ollevier, Org. Biomol. Chem. 2017, 15, 5441-5456;
C. Damiano, P. Sonzini, E. Gallo, Chem. Soc. Rev. 2020, 49, 4867-4905;
M.-Y. Huang, S.-F. Zhu, Chem. Sci. 2021, 12, 15790-15801;
V. Carreras, N. Tanbouza, T. Ollevier, Synthesis 2020, 53, 79-94;
Z. Liu, J. Wang, J. Org. Chem. 2013, 78, 10024-10030;
Y. He, Z. Huang, K. Wu, J. Ma, Y.-G. Zhou, Z. Yu, Chem. Soc. Rev. 2022, 51, 2759-2852;
Y. Xia, D. Qiu, J. Wang, Chem. Rev. 2017, 117, 13810-13889.
X. Wang, X. Wang, J. Wang, Tetrahedron 2019, 75, 949-964;
J.-H. Lin, J.-C. Xiao, Acc. Chem. Res. 2020, 53, 1498-1510;
L. Mertens, R. M. Koenigs, Org. Biomol. Chem. 2016, 14, 10547-10556;
K. Fuchibe, J. Ichikawa, Chem. Commun. 2023, 59, 2532-2540.
W. Zhou, W.-J. Pan, J. Chen, M. Zhang, J.-H. Lin, W. Cao, J.-C. Xiao, Chem. Commun. 2021, 57, 9316-9329;
A. D. Dilman, V. V. Levin, Acc. Chem. Res. 2018, 51, 1272-1280;
C. Ni, J. Hu, Synthesis 2014, 46, 842-863;
X. Ma, J. Su, Q. Song, Acc. Chem. Res. 2023, 56, 592-607;
P. K. Mykhailiuk, R. M. Koenigs, Chem. Eur. J. 2019, 25, 6053-6063.
D. L. S. Brahms, W. P. Dailey, Chem. Rev. 1996, 96, 1585-1632.
J. Decaens, S. Couve-Bonnaire, A. B. Charette, T. Poisson, P. Jubault, Chem. Eur. J. 2021, 27, 2935-2962;
M. Fedoryński, Chem. Rev. 2003, 103, 1099-1132;
A. Pons, T. Poisson, X. Pannecoucke, A. B. Charette, P. Jubault, Synthesis 2016, 48, 4060-4071;
L. Ielo, V. Pillari, M. Miele, D. Castiglione, V. Pace, Synlett 2021, 32, 551-560;
M. Colella, P. Musci, M. Andresini, M. Spennacchio, L. Degennaro, R. Luisi, Org. Biomol. Chem. 2022, 20, 4669-4680;
A. Pons, L. Delion, T. Poisson, A. B. Charette, P. Jubault, Acc. Chem. Res. 2021, 54, 2969-2990.
M. Born, S. Ingemann, N. M. M. Nibbering, J. Am. Chem. Soc. 1994, 116, 7210-7217.
M. Schwartz, P. Marshall, J. Phys. Chem. A 1999, 103, 7900-7906.
V. Fasano, N. Winter, A. Noble, V. K. Aggarwal, Angew. Chem. Int. Ed. 2020, 59, 8502-8506.
R. A. Moss, J. Phys. Org. Chem. 2010, 23, 293-299.
J. C. Poutsma, J. A. Paulino, R. R. Squires, J. Phys. Chem. A 1997, 101, 5327-5336.
M. K. Gilles, K. M. Ervin, J. Ho, W. C. Lineberger, J. Phys. Chem. 1992, 96, 1130-1141.
T. Suzuki, S. Saito, E. Hirota, J. Mol. Spectrosc. 1981, 90, 447-459.
Y.-N. Tang, F. S. Rowland, J. Am. Chem. Soc. 1967, 89, 6420-6427.
T. Marolewski, N. C. Yang, Chem. Commun. (London) 1967, 1225-1226, https://doi.org/10.1039/C19670001225.
M. Schlosser, G. Heinz, Angew. Chem. Int. Ed. Engl. 1968, 7, 820-821.
A. S. Konev, M. S. Novikov, A. F. Khlebnikov, Tetrahedron Lett. 2005, 46, 8337-8340.
J. Nishimura, J. Furukawa, J. Chem. Soc. D 1971, 1375-1376, https://doi.org/10.1039/C29710001375.
O. Tamura, M. Hashimoto, Y. Kobayashi, T. Katoh, K. Nakatani, M. Kamada, I. Hayakawa, T. Akiba, S. Terashima, Tetrahedron Lett. 1992, 33, 3483-3486.
P. Knochel, in Encyclopedia of Reagents for Organic Synthesis (EROS), 2001.
N. Kawabata, M. Tanimoto, S. Fujiwara, Tetrahedron 1979, 35, 1919-1923.
L.-P. B. Beaulieu, J. F. Schneider, A. B. Charette, J. Am. Chem. Soc. 2013, 135, 7819-7822.
C. Navuluri, A. B. Charette, Org. Lett. 2015, 17, 4288-4291.
S. Monticelli, M. Colella, V. Pillari, A. Tota, T. Langer, W. Holzer, L. Degennaro, R. Luisi, V. Pace, Org. Lett. 2019, 21, 584-588.
M. Colella, A. Tota, Y. Takahashi, R. Higuma, S. Ishikawa, L. Degennaro, R. Luisi, A. Nagaki, Angew. Chem. Int. Ed. 2020, 59, 10924-10928.
M. Colella, A. Tota, A. Großjohann, C. Carlucci, A. Aramini, N. S. Sheikh, L. Degennaro, R. Luisi, Chem. Commun. 2019, 55, 8430-8433.
A. Sperga, D. Zacs, J. Veliks, Org. Lett. 2022, 24, 4474-4478.
A. Nouaille, J. Lorkowski, X. Pannecoucke, M. Mauduit, T. Poisson, S. Couve-Bonnaire, ACS Catal. 2021, 11, 12307-12323;
G. Landelle, M. Bergeron, M.-O. Turcotte-Savard, J.-F. Paquin, Chem. Soc. Rev. 2011, 40, 2867-2908;
B. Zajc, R. Kumar, Synthesis 2010, 2010, 1822-1836;
Q. Luo, X. Wang, J. Hu, Tetrahedron 2022, 113, 132694;
H. Yanai, T. Taguchi, Eur. J. Org. Chem. 2011, 2011, 5939-5954.
W. Zhang, J. Hu, Adv. Synth. Catal. 2010, 352, 2799-2804.
X. Shen, W. Zhang, L. Zhang, T. Luo, X. Wan, Y. Gu, J. Hu, Angew. Chem. Int. Ed. 2012, 51, 6966-6970.
R. Melngaile, J. Veliks, Synthesis 2021, 53, 4549-4558;
R. Melngaile, J. Veliks, in Encyclopedia of Reagents for Organic Synthesis (EROS), pp. 1-4.
J. Veliks, A. Kazia, Chem. Eur. J. 2019, 25, 3786-3789.
R. Melngaile, A. Sperga, K. K. Baldridge, J. Veliks, Org. Lett. 2019, 21, 7174-7178.
A. Kazia, R. Melngaile, A. Mishnev, J. Veliks, Org. Biomol. Chem. 2020, 18, 1384-1388.
A. Sperga, R. Melngaile, A. Kazia, S. Belyakov, J. Veliks, J. Org. Chem. 2021, 86, 3196-3212.
A. Sperga, A. Kazia, J. Veliks, Org. Biomol. Chem. 2021, 19, 2688-2691.
C.-C. Hu, W.-Q. Hu, X.-H. Xu, F.-L. Qing, J. Fluorine Chem. 2021, 242, 109695.
M. Reichel, K. Karaghiosoff, Angew. Chem. Int. Ed. 2020, 59, 12268-12281.
E. Sun, R. Li, Q. Sun, C. Wei, H. Xu, B. Yan, J. Phys. Chem. A 2012, 116, 10435-10440;
G. B. Bacskay, Mol. Phys. 2015, 113, 1608-1617;
E. Sun, J. Zhang, R. Li, Q. Sun, C. Wei, H. Xu, B. Yan, Int. J. Quantum Chem. 2014, 114, 66-73;
K. K. Irikura, W. A. Goddard, III, J. L. Beauchamp, J. Am. Chem. Soc. 1992, 114, 48-51.
R. A. Moss, M. Zhang, K. Krogh-Jespersen, Org. Lett. 2010, 12, 3476-3479;
M. Zhang, R. A. Moss, J. Thompson, K. Krogh-Jespersen, J. Org. Chem. 2012, 77, 843-850.
A. P. Thankachan, K. S. Sindhu, K. K. Krishnan, G. Anilkumar, Org. Biomol. Chem. 2015, 13, 8780-8802.
A. A. Andrianova, Y. D. Maslova, M. A. Novikov, S. E. Semenov, O. M. Nefedov, J. Fluorine Chem. 2018, 209, 49-55.
M. Goswami, B. de Bruin, W. I. Dzik, Chem. Commun. 2017, 53, 4382-4385;
P. S. Nosik, S. V. Ryabukhin, O. O. Grygorenko, D. M. Volochnyuk, Adv. Synth. Catal. 2018, 360, 4104-4114.
D. Chen, Z. Fan, L. Huang, K. Gao, P. Xiao, C. Ni, J. Hu, Chem. Commun. 2021, 57, 319-322.
C. Barrett, V. Krishnamurti, X. Ispizua-Rodriguez, Z. Zhu, C. J. Koch, G. K. Surya Prakash, Org. Lett. 2022, 24, 5417-5421;
C. Aouf, M. Santelli, Tetrahedron Lett. 2011, 52, 688-691.
R. Bychek, P. K. Mykhailiuk, Angew. Chem. Int. Ed. 2022, 61, e202205103.
P. K. Mykhailiuk, Org. Biomol. Chem. 2019, 17, 2839-2849;
G. M. Locke, S. S. R. Bernhard, M. O. Senge, Chem. Eur. J. 2019, 25, 4590-4647.
C. Recsei, Y. Barda, Beilstein J. Org. Chem. 2021, 17, 813-818.
L. Trump, A. Lemos, B. Lallemand, P. Pasau, J. Mercier, C. Lemaire, A. Luxen, C. Genicot, Angew. Chem. Int. Ed. 2019, 58, 13149-13154.
R. Mathias, P. Weyerstahl, Chem. Ber. 1979, 112, 3041-3053;
P. Weyerstahl, R. Mathias, G. Blume, Tetrahedron Lett. 1973, 14, 611-612.
Z. Fang, D. B. Cordes, A. M. Z. Slawin, D. O′Hagan, Chem. Commun. 2019, 55, 10539-10542.
E. David, S. Couve-Bonnaire, P. Jubault, X. Pannecoucke, Tetrahedron 2013, 69, 11039-11055;
A. Tarui, K. Sato, M. Omote, I. Kumadaki, A. Ando, Adv. Synth. Catal. 2010, 352, 2733-2744.
A. Tarui, N. Kawashima, K. Sato, M. Omote, A. Ando, Tetrahedron Lett. 2010, 51, 4246-4249.
G. Lemonnier, L. Zoute, J.-C. Quirion, P. Jubault, Org. Lett. 2010, 12, 844-846.
P. Ivashkin, S. Couve-Bonnaire, P. Jubault, X. Pannecoucke, Org. Lett. 2012, 14, 2270-2273.
P. Ivashkin, S. Couve-Bonnaire, P. Jubault, X. Pannecoucke, Org. Lett. 2012, 14, 5130-5133.
G. Lemonnier, C. Lion, J.-C. Quirion, J.-P. Pin, C. Goudet, P. Jubault, Bioorg. Med. Chem. 2012, 20, 4716-4726;
G. Milanole, S. Couve-Bonnaire, J.-F. Bonfanti, P. Jubault, X. Pannecoucke, J. Org. Chem. 2013, 78, 212-223.
T. Ferrary, E. David, G. Milanole, T. Besset, P. Jubault, X. Pannecoucke, Org. Lett. 2013, 15, 5598-5601.
J. Czaban-Jóźwiak, R. Loska, M. Mąkosza, J. Org. Chem. 2016, 81, 11751-11757.
A. Zasada, J. Brześkiewicz, D. Antoniak, M. Bechcicka, R. Loska, M. Mąkosza, Org. Biomol. Chem. 2023, 21, 994-999.
M. Kirihara, T. Ogata, A. Itou, S. Naito, M. Kishida, K. Yamazaki, H. Tabata, H. Takahashi, Chem. Lett. 2013, 42, 1377-1379.
E. A. Ilin, V. O. Smirnov, A. D. Dilman, J. Fluorine Chem. 2022, 261-262, 110025.
R. A. Moss, Y. Shen, L. Wang, K. Krogh-Jespersen, Org. Lett. 2011, 13, 4752-4754.
R. A. Moss, L. Wang, R. R. Sauers, Tetrahedron Lett. 2007, 48, 5551-5554.
J. H. Rigby, M. Aasmul, Heterocycles 2004, 62, 143-147.
H. Wang, R.-Y. Yang, B. Xu, Chem. Eur. J. 2022, 28, e202104364.
S. Guo, W. Sun, J. W. Tucker, K. D. Hesp, N. K. Szymczak, Chem. Eur. J. 2023, 29, e202203578.
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, Russ. Chem. Bull. 2002, 51, 1237-1253.
C. B. A. L. Bagdasarian, R. A. Craig II, J. De Vicente Fidalgo, A. A. Estrada, B. M. Fox, C. Hu, B. J. Huffman, K. W. Lexa, L. G. Nilewski, M. Osipov, A. Thottumkara (Denali Therapeutics inc.), WO2022232632, 2022.
M. E. B. D. R. Anderson, K. J. Curran, C. M. Dehnhardt, L. K. Gavrin, J. A. Goldberg, S. Han, D. Hepworth, H.-C. Huang, A. Lee, K. L. Lee, F. E. Lovering, M. D. Lowe, J. P. Mathias, N. Papaioannou, A. Patny, B. S. Pierce, E. Saiah, J. W. Strohbach, J. D. Trzupek, R. Vargas, X. Wang, S. W. Wright, C. W. Zapf (Pfizer inc.), WO2015150995, 2015.
J. Veliks, M. Videja, A. Kinens, R. Bobrovs, M. Priede, J. Kuka, ACS Med. Chem. Lett. 2020, 11, 2146-2150.
G. Milanole, F. Andriessen, G. Lemonnier, M. Sebban, G. Coadou, S. Couve-Bonnaire, J.-F. Bonfanti, P. Jubault, X. Pannecoucke, Org. Lett. 2015, 17, 2968-2971.
R. Melngaile, M. Videja, J. Kuka, A. Kinens, D. Zacs, J. Veliks, Org. Lett. 2023, 25, 2280-2284.