Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me₃SiCF₂SO₂Ph and PhSO₂CF₂H reagents catalyzed by chiral quaternary ammonium salts

Scholarly Works

• Bacheley, L.; Ravindra, R.; Guillamot, G.; Phansavath, P.; Ratovelomanana‐Vidal, V. Access to Enantioenriched β‐Hydroxy gem‐Difluorinated Heterocyclic and Acyclic Derivatives through Rh(III)‐Catalyzed Asymmetric Transfer Hydrogenation. Advanced Synthesis & Catalysis 2024, 366, 1019–1023. doi:10.1002/adsc.202301294
• Zou, H.-N.; Huang, M.-L.; Huang, M.-Y.; Su, Y.-X.; Zhang, J.-W.; Zhang, X.-Y.; Zhu, S.-F. Chiral gem-difluoroalkyl reagents: gem-difluoroalkyl propargylic borons and gem-difluoroalkyl α-allenols. Chemical science 2023, 14, 9186–9190. doi:10.1039/d3sc03266c
• Sanz-Marco, A.; Esperilla, D.; Montesinos-Magraner, M.; Vila, C.; Muñoz, M. C.; Pedro, J. R.; Blay, G. A Cu-BOX catalysed enantioselective Mukaiyama-aldol reaction with difluorinated silyl enol ethers and acylpyridine N-oxides. Organic & biomolecular chemistry 2023, 21, 345–350. doi:10.1039/d2ob01763f
• Cai, X.; Xu, J.; Cui, X.; Qu, J.; Sun, W.; Hu, J.; Zhao, S.; Chen, W.-H.; Li, H.; Wu, J.-Q. Synthesis of difluoromethyl carbinols from the Friedel–Crafts reaction of electron-rich arenes with difluorovinyl arylsulfonates. Organic Chemistry Frontiers 2022, 9, 6273–6280. doi:10.1039/d2qo01277d
• Yang, J.; Ponra, S.; Li, X.; Peters, B. B. C.; Massaro, L.; Zhou, T.; Andersson, P. G. Catalytic enantioselective synthesis of fluoromethylated stereocenters by asymmetric hydrogenation. Chemical science 2022, 13, 8590–8596. doi:10.1039/d2sc02685f
• Uno, H.; Kawai, K.; Araki, T.; Shiro, M.; Shibata, N. Enantio-, Diastereo- and Regioselective Synthesis of Chiral Cyclic and Acyclic gem-Difluoromethylenes by Palladium-Catalyzed [4+2] Cycloaddition. Angewandte Chemie (International ed. in English) 2022, 61, e202117635. doi:10.1002/anie.202117635
• Uno, H.; Kawai, K.; Araki, T.; Shiro, M.; Shibata, N. Enantio‐, Diastereo‐ and Regioselective Synthesis of Chiral Cyclic and Acyclic gem‐Difluoromethylenes by Palladium‐Catalyzed [4+2] Cycloaddition. Angewandte Chemie 2022, 134. doi:10.1002/ange.202117635
• Wu, C.; Shen, X.; Dai, J.-J.; Xu, J.; Xu, H.-J. Synthesis of (benzenesulfonyl)difluoromethyl thioethers from ((difluoromethyl)sulfonyl)benzene and organothiocyanates generated in situ. Organic & biomolecular chemistry 2021, 19, 7607–7610. doi:10.1039/d1ob01215k
• Gao, F.; Li, B.; Wang, Y.; Chen, Q.; Li, Y.; Wang, K.; Yan, W. Stereoselective synthetic strategies of stereogenic carbon centers featuring a difluoromethyl group. Organic Chemistry Frontiers 2021, 8, 2799–2819. doi:10.1039/d1qo00032b
• Ispizua-Rodriguez, X.; Barrett, C.; Krishamurti, V.; Prakash, G. K. S. Silicon-based difluoromethylations, difluoromethylenations, pentafluoroethylations, and related fluoroalkylations. The Curious World of Fluorinated Molecules; Elsevier, 2021; pp 117–218. doi:10.1016/b978-0-12-819874-2.00012-6
• Miller, E. G.; Kim, S.; Gibson, K.; Derrick, J. S.; Toste, F. D. Regio- and Enantioselective Bromocyclization of Difluoroalkenes as a Strategy to Access Tetrasubstituted Difluoromethylene-Containing Stereocenters. Journal of the American Chemical Society 2020, 142, 8946–8952. doi:10.1021/jacs.0c02331
• Xie, Q.; Hu, J. Emerging Fluorinated Motifs; Wiley, 2020; pp 89–117. doi:10.1002/9783527824342.ch3
• Huang, W.-S.; Delcourt, M.-L.; Pannecoucke, X.; Charette, A. B.; Poisson, T.; Jubault, P. Catalytic Asymmetric Synthesis of α,α-Difluoromethylated and α-Fluoromethylated Tertiary Alcohols. Organic letters 2019, 21, 7509–7513. doi:10.1021/acs.orglett.9b02792
• Batisse, C.; Dávila, M. F. C.; Castello, M.; Messara, A.; Bertrand, V.; Gilbert, M.; Panossian, A.; Hanquet, G.; Leroux, F. R. Efficient asymmetric synthesis of aryl difluoromethyl sulfoxides and their use to access enantiopure α-difluoromethyl alcohols. Tetrahedron 2019, 75, 3063–3079. doi:10.1016/j.tet.2019.04.037
• Gong, Y.; Yu, J.-S.; Hao, Y.-J.; Zhou, Y.; Zhou, J. Catalytic Enantioselective Aldol‐Type Reaction Using α‐Fluorinated Enolates. Asian Journal of Organic Chemistry 2019, 8, 610–626. doi:10.1002/ajoc.201900071
• Batisse, C.; Panossian, A.; Hanquet, G.; Leroux, F. R. Access towards enantiopure α,α-difluoromethyl alcohols by means of sulfoxides as traceless chiral auxiliaries. Chemical communications (Cambridge, England) 2018, 54, 10423–10426. doi:10.1039/c8cc05571h
• Zhu, Y.-J.; Lei, Z.-L.; Huang, D.-K.; Bo, L.; Liu, Z.-J.; Hu, X.-J.; Liu, J.-T. Decarboxylative difluoromethylation of aldehydes with PhSO2CF2COOK: A facile and efficient access to difluoromethylated carbinols. Tetrahedron Letters 2018, 59, 3184–3187. doi:10.1016/j.tetlet.2018.07.021
• Liu, J.; Ding, W.; Zhou, Q.-Q.; Liu, D.; Lu, L.-Q.; Xiao, W.-J. Enantioselective Di-/Perfluoroalkylation of β-Ketoesters Enabled by Cooperative Photoredox/Nickel Catalysis. Organic letters 2018, 20, 461–464. doi:10.1021/acs.orglett.7b03826
• Cui, B.; Sun, H.; Xu, Y.; Duan, L.; Li, Y. MgCl2-catalyzed trifluoromethylation of carbonyl compounds using (trifluoromethyl)trimethylsilane as the trifluoromethylating agent. Tetrahedron 2017, 73, 6754–6762. doi:10.1016/j.tet.2017.10.021
• Jiang, F.; Ni, C.; Hu, J. Efficient nucleophilic difluoromethylation of aldehydes with (phenylsulfonyl)difluoromethylzinc and (phenylsulfonyl)difluoromethylcadmium reagents. Journal of Fluorine Chemistry 2017, 198, 67–75. doi:10.1016/j.jfluchem.2016.12.005

Explore citations to this article at