Deoxytrifluoromethylation/aromatization of cyclohexan(en)ones to access highly substituted trifluoromethyl arenes.
Journal
Nature communications
ISSN: 2041-1723
Titre abrégé: Nat Commun
Pays: England
ID NLM: 101528555
Informations de publication
Date de publication:
09 Sep 2024
09 Sep 2024
Historique:
received:
12
07
2024
accepted:
26
08
2024
medline:
10
9
2024
pubmed:
10
9
2024
entrez:
9
9
2024
Statut:
epublish
Résumé
Trifluoromethyl arenes (Ar-CF
Identifiants
pubmed: 39251584
doi: 10.1038/s41467-024-52035-9
pii: 10.1038/s41467-024-52035-9
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
7882Subventions
Organisme : NCI NIH HHS
ID : P30 CA023168
Pays : United States
Organisme : National Science Foundation (NSF)
ID : CHE-1625543
Organisme : U.S. Department of Health & Human Services | NIH | National Institute of General Medical Sciences (NIGMS)
ID : GM124661
Informations de copyright
© 2024. The Author(s).
Références
Dolbier, W. R. Fluorine chemistry at the millennium. J. Fluor. Chem. 126, 157–163 (2005).
doi: 10.1016/j.jfluchem.2004.09.033
Maienfisch, P. & Hall, R. G. The Importance of Fluorine in the Life Science Industry. Chimia 58, 93 (2004).
doi: 10.2533/000942904777678091
Richardson, P. Fluorination methods for drug discovery and development. Expert Opin. Drug Discov. 11, 983–999 (2016).
pubmed: 27548817
doi: 10.1080/17460441.2016.1223037
Shah, P. & Westwell, A. D. The role of fluorine in medicinal chemistry. J. Enzym. Inhibition Medicinal Chem. 22, 527–540 (2007).
doi: 10.1080/14756360701425014
Jeschke, P. The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection. ChemBioChem 5, 570–589 (2004).
doi: 10.1002/cbic.200300833
Berger, R., Resnati, G., Metrangolo, P., Weber, E. & Hulliger, J. Organic fluorine compounds: a great opportunity for enhanced materials properties. Chem. Soc. Rev. 40, 3496 (2011).
pubmed: 21448484
doi: 10.1039/c0cs00221f
Inoue, M., Sumii, Y. & Shibata, N. Contribution of Organofluorine Compounds to Pharmaceuticals. ACS Omega 5, 10633–10640 (2020).
pubmed: 32455181
pmcid: 7240833
doi: 10.1021/acsomega.0c00830
Ogawa, Y., Tokunaga, E., Kobayashi, O., Hirai, K. & Shibata, N. Current Contributions of Organofluorine Compounds to the Agrochemical Industry. iScience 23, 101467 (2020).
pubmed: 32891056
pmcid: 7479632
doi: 10.1016/j.isci.2020.101467
Studer, A. A “Renaissance” in Radical Trifluoromethylation. Angew. Chem. Int. Ed. 51, 8950–8958 (2012).
doi: 10.1002/anie.201202624
Wu, X., Neumann, H. & Beller, M. Recent Developments on the Trifluoromethylation of (Hetero)Arenes. Chem.– Asian J. 7, 1744–1754 (2012).
pubmed: 22715145
doi: 10.1002/asia.201200211
Liu, T. & Shen, Q. Progress in Copper-Mediated Formation of Trifluoromethylated Arenes. Eur. J. Org. Chem. 2012, 6679–6687 (2012).
doi: 10.1002/ejoc.201200648
Tomashenko, O. A. & Grushin, V. V. Aromatic Trifluoromethylation with Metal Complexes. Chem. Rev. 111, 4475–4521 (2011).
pubmed: 21456523
doi: 10.1021/cr1004293
Li, G., Zhang, C., Song, C. & Ma, Y. Progress in Copper-Catalyzed Trifluoromethylation. Beilstein J. Org. Chem. 14, 155–181 (2018).
pubmed: 29441139
pmcid: 5789444
doi: 10.3762/bjoc.14.11
Mandal, D., Maji, S., Pal, T., Sinha, S. K. & Maiti, D. Recent Advances in Transition Metal- Mediated Trifluoromethylation Reactions. Chem. Commun. 58, 10442–10468 (2022).
doi: 10.1039/D2CC04082D
Swarts, F. Etude Sur Le Fluo Chloroforme. Acad. R. Belgium 24, 474 (1892).
Banks, R. E. & Tatlow, J. C. Synthesis of C–F Bonds: The Pioneering Years, 1835 – 1940. J. Fluor. Chem. 33, 71–108 (1986).
doi: 10.1016/S0022-1139(00)85272-0
Oishi, M., Kondo, H. & Amii, H. Aromatic Trifluoromethylation Catalytic in Copper. Chem. Commun. 14, 1909–1911 (2009).
doi: 10.1039/b823249k
Cho, E. J. et al. The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides. Science 328, 1679–1681 (2010).
pubmed: 20576888
pmcid: 3005208
doi: 10.1126/science.1190524
Le, C., Chen, T. Q., Liang, T., Zhang, P. & MacMillan, D. W. C. A Radical Approach to the Copper Oxidative Addition Problem: Trifluoromethylation of Bromoarenes. Science 360, 1010–1014 (2018).
pubmed: 29853683
pmcid: 6607890
doi: 10.1126/science.aat4133
Dubinina, G. G., Furutachi, H. & Vicic, D. A. Active Trifluoromethylating Agents from Well-Defined Copper(I)−CF
pubmed: 18543912
doi: 10.1021/ja802946s
Hu, W., Pan, S., Xu, X., Vicic, D. A. & Qing, F. Nickel‐Mediated Trifluoromethylation of Phenol Derivatives by Aryl C−O Bond Activation. Angew. Chem. Int. Ed. 59, 16076–16082 (2020).
doi: 10.1002/anie.202004116
Morimoto, H., Tsubogo, T., Litvinas, N. D. & Hartwig, J. F. A Broadly Applicable Copper Reagent for Trifluoromethylations and Perfluoroalkylations of Aryl Iodides and Bromides. Angew. Chem. Int. Ed. 123, 3877–3882 (2011).
doi: 10.1002/ange.201100633
Koike, T. & Akita, M. Trifluoromethylation by Visible-Light-Driven Photoredox Catalysis. Top. Catal. 57, 967–974 (2014).
doi: 10.1007/s11244-014-0259-7
Ji, Y. et al. Innate C–H Trifluoromethylation of Heterocycles. Proc. Natl Acad. Sci. 108, 14411–14415 (2011).
pubmed: 21844378
pmcid: 3167544
doi: 10.1073/pnas.1109059108
Nagib, D. A. & Macmillan, D. W. C. Trifluoromethylation of Arenes and Heteroarenes by Means of Photoredox Catalysis. Nature 480, 224–228 (2011).
pubmed: 22158245
pmcid: 3310175
doi: 10.1038/nature10647
Campbell, B. M. et al. Electrophotocatalytic perfluoroalkylation by LMCT excitation of Ag(II) perfluoroalkyl carboxylates. Science 383, 279–284 (2024).
Smith, W. C. et al. Fluorination Reactions Of Sulfur Tetrafluoride. J. Am. Chem. Soc. 81, 3165–3166 (1959).
doi: 10.1021/ja01521a086
Malapit, C. A., Ichiishi, N. & Sanford, M. S. Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides. Org. Lett. 19, 4142–4145 (2017).
pubmed: 28723158
pmcid: 5565168
doi: 10.1021/acs.orglett.7b02024
de Azambuja, F., Lovrien, S. M., Ross, P., Ambler, B. R. & Altman, R. A. Catalytic One-Step Deoxytrifluoromethylation of Alcohols. J. Org. Chem. 84, 2061–2071 (2019).
pubmed: 30632749
pmcid: 6387626
doi: 10.1021/acs.joc.8b03072
Zhu, L., Liu, S., Douglas, J. T. & Altman, R. A. Copper-Mediated Deoxygenative Trifluoromethylation of Benzylic Xanthates: Generation of a C–CF
doi: 10.1002/chem.201302328
Liu, Z.-Y. & Cook, S. P. Interrupting the Barton–McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of O-Alkyl Thiocarbonates. Org. Lett. 23, 808–813 (2021).
pubmed: 33443440
pmcid: 9558134
doi: 10.1021/acs.orglett.0c04039
Intermaggio, N. E., Millet, A., Davis, D. L. & MacMillan, D. W. C. Deoxytrifluoromethylation of Alcohols. J. Am. Chem. Soc. 144, 11961–11968 (2022).
pubmed: 35786873
pmcid: 9676087
doi: 10.1021/jacs.2c04807
Duan, J.-X. & Chen, Q.-Y. Novel synthesis of 2,2,2-Trifluoroethyl Compounds from Homoallylic alcohols: a Copper (I) Iodide-Initiated Trifluoromethyl–Dehydroxylation Process. J. Chem. Soc. Perkin Trans. 1, 725–730 (1994).
doi: 10.1039/P19940000725
Takechi, N., Ait-Mohand, S., Medebielle, M. & Dolbier, W. R. Novel Nucleophilic Trifluoromethylation of Vicinal Diol Cyclic Sulfates. Org. Lett. 4, 4671–4672 (2002).
pubmed: 12489957
doi: 10.1021/ol0270374
Tan, L., Chen, C., Larsen, R. D., Verhoeven, T. R. & Reider, P. J. An Efficient Asymmetric Synthesis of a Potent COX-2 inhibitor L-784,512. Tetrahedron Lett. 39, 3961–3964 (1998).
doi: 10.1016/S0040-4039(98)00735-7
Sorrentino, J. P., Ambler, B. R. & Altman, R. A. Late-Stage Conversion of a Metabolically Labile Aryl Methyl Ether-Containing Natural Product to Fluoroalkyl Analogues. J. Org. Chem. 85, 5416–5427 (2020).
pubmed: 32191836
pmcid: 7358012
doi: 10.1021/acs.joc.0c00125
Ramaiah, P., Krishnamurti, R. & Surya Prakash, G. K. 1-trifluoromethyl-1-cyclohexanol. Org. Syntheses 72, 232 (1995).
doi: 10.15227/orgsyn.072.0232
Clive, D. L. J. & Pham, M. P. Conversion of Weinreb Amides into Benzene Rings Incorporating the Amide Carbonyl Carbon. J. Org. Chem. 74, 1685–1690 (2009).
pubmed: 19173556
doi: 10.1021/jo802629w
Batista, V. S., Crabtree, R. H., Konezny, S. J., Luca, O. R. & Praetorius, J. M. Oxidative Functionalization of Benzylic C–H Bonds by DDQ. N. J. Chem. 36, 1141 (2012).
doi: 10.1039/c2nj40021a
Carcenac, Y., Tordeux, M., Wakselman, C. & Diter, P. Convenient Synthesis of Fluorinated Alkanes and Cycloalkanes by Hydrogenation of Perfluoroalkylalkenes Under Ultrasound Irradiation. J. Fluor. Chem. 126, 1347–1355 (2005).
doi: 10.1016/j.jfluchem.2005.07.006
Trost, B. M. & Metzner, P. J. Reaction of Olefins with Palladium Trifluoroacetate. J. Am. Chem. Soc. 102, 3572–3577 (1980).
doi: 10.1021/ja00530a042
Boyd, D. R. et al. Chemoenzymatic Synthesis of Trans-Dihydrodiol Derivatives of Monosubstituted Benzenes from the Corresponding cis-Dihydrodiol Isomers. Org. Biomolecular Chem. 5, 514 (2007).
doi: 10.1039/b616100f
Amongero, M., Visnovezky, D. & Kaufman, T. S. Chiral Auxiliary-Mediated Enantioenrichment of (±)-Ibuprofen, under Steglich Conditions, with Secondary Alcohols Derived from (R)-Carvone. J. Braz. Chem. Soc. 21, 1017–1036 (2010).
doi: 10.1590/S0103-50532010000600011
Burrows, J., Kamo, S. & Koide, K. Scalable Birch Reduction with Lithium and Ethylenediamine in Tetrahydrofuran. Science 374, 741–746 (2021).
pubmed: 34735232
doi: 10.1126/science.abk3099
Samser, S., Biswal, P., Meher, S. K. & Venkatasubbaiah, K. Palladium Mediated One-pot Synthesis of 3-Aryl-cyclohexenones and 1,5-Diketones from Allyl Alcohols and Aryl Ketones. Org. Biomolecular Chem. 19, 1386–1394 (2021).
doi: 10.1039/D0OB02515A
Chen, J. et al. Synthesis of 3,4,5‐Triarylcyclohexanones from Dienones and 2‐Methylquinolines Based on a [5+1] Annulation. ChemistrySelect 6, 10802–10805 (2021).
doi: 10.1002/slct.202103317
Tang, L., Luo, Y., Xue, J.-W., He, Y.-H. & Guan, Z. Highly Enantioselective Michael-Aldol-Dehydration Reaction for the Synthesis of chiral 3,5-Diaryl-cyclohexenones Catalyzed by Primary Amine. Tetrahedron 73, 1114–1119 (2017).
doi: 10.1016/j.tet.2017.01.004