Gribble, G. W. A recent survey of naturally occurring organohalogen compounds. Environ. Chem. 12, 396–405 (2015).ArticleÂ
CASÂ
Google ScholarÂ
Huchet, Q. A. et al. Fluorination patterning: a study of structural motifs that impact physicochemical properties of relevance to drug discovery. J. Med. Chem. 58, 9041–9060 (2015).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Fauber, B. P. et al. Structure-based design of substituted hexafluoroisopropanol-arylsulfonamides as modulators of RORc. Bioorg. Med. Chem. Lett. 23, 6604–6609 (2013).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Mimura, H., Kawada, K., Yamashita, T., Sakamoto, T. & Kikugawa, Y. Trifluoroacetaldehyde: a useful industrial bulk material for the synthesis of trifluoromethylated amino compounds. J. Fluor. Chem. 131, 477–486 (2010).ArticleÂ
CASÂ
Google ScholarÂ
Blackburn, G. M. & Kent, D. E. Monofluoro- and difluoromethylenebisphosphonic acids: isopolar analogues of pyrophosphoric acid. J. Chem. Soc. Chem. Commun. 1981, 930–932 (1981).ArticleÂ
Google ScholarÂ
Furuya, T., Kamlet, A. S. & Ritter, T. Catalysis for fluorination and trifluoromethylation. Nature 473, 470–477 (2011).ArticleÂ
ADSÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Tomashenko, O. A. & Grushin, V. V. Aromatic trifluoromethylation with metal complexes. Chem. Rev. 111, 4475–4521 (2011).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Yang, X., Wu, T., Phipps, R. J. & Toste, F. D. Advances in catalytic enantioselective fluorination, mono-, di- and trifluoromethylation, and trifluoromethylthiolation reactions. Chem. Rev. 115, 826–870 (2015).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Zhang, F., Xiao, Y.-L. & Zhang, X. Transition-metal (Cu, Pd, Ni)-catalyzed difluoroalkylation via cross-coupling with difluoroalkyl halides. Acc. Chem. Res. 51, 2264–2278 (2018).ArticleÂ
PubMedÂ
Google ScholarÂ
Al-Maharik, N. & O’Hagan, D. Organofluorine chemistry:deoxyfluorination reagents for C−F bond synthesis. Aldrichim. Acta 44, 65–75 (2011).CASÂ
Google ScholarÂ
Levin, V. V., Zemtsov, A. A., Struchkova, M. I. & Dilman, A. D. Reactions of difluorocarbene with organozinc reagents. Org. Lett. 15, 917–919 (2013).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Dilman, A. D. & Levin, V. V. Difluorocarbene as a building block for consecutive bond-forming reactions. Acc. Chem. Res. 51, 1272–1280 (2018).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Zeng, X., Li, Y., Min, Q.-Q., Xue, X.-X. & Zhang, X. Copper-catalysed difluorocarbene transfer enables modular synthesis. Nat. Chem. 15, 1064–1073 (2023).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Yue, W.-J., Day, C. S., Rucinski, A. J. B. & Martin, R. Catalytic hydrodifluoroalkylation of unactivated olefins. Org. Lett. 24, 5109–5114 (2022).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Ren, X., Gao, X., Min, Q.-Q., Zhang, S. & Zhang, X. (Fluoro)alkylation of alkenes promoted by photolysis of alkylzirconocenes. Chem. Sci. 13, 3454–3460 (2022).Giese, B. Formation of CC bonds by addition of free radicals to alkenes. Angew. Chem. Int. Ed. 22, 753–764 (1983).ArticleÂ
Google ScholarÂ
Lo, J. C., Yabe, Y. & Baran, P. S. A practical and catalytic reductive olefin coupling. J. Am. Chem. Soc 136, 1304–1307 (2014).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Lo, J. C., Gui, J., Yabe, Y., Pan, C.-M. & Baran, P. S. Functionalized olefin cross-coupling to construct carbon−carbon bonds. Nature 516, 343–348 (2014).ArticleÂ
ADSÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Crossley, S. W. M., Obradors, C., Martinez, R. M. & Shenvi, R. A. Mn-, Fe-, and co-catalyzed radical hydrofunctionalizations of olefins. Chem. Rev. 116, 8912–9000 (2016).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Green, S. A. et al. The high chemofidelity of metal-catalyzed hydrogen atom transfer. Acc. Chem. Res. 51, 2628–2640 (2018).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Zhou, W., Dmitriev, I. A. & Melchiorre, P. Reductive cross-coupling of olefins via a radical pathway. J. Am. Chem. Soc. 145, 25098–25102 (2023).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Sarkar, S., Ghosh, S., Kurandina, D., Noffel, Y. & Gevorgyan, V. Enhanced excited-state hydricity of Pd–H allows for unusual head-to-tail hydroalkenylation of alkenes. J. Am. Chem. Soc. 145, 12224–12232 (2023).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Rao, C., Zhang, T., Liu, H. & Huang, H. Double alkyl–alkyl bond construction across alkenes enabled by nickel electron-shuttle catalysis. Nat. Catal. 6, 847–857 (2023).ArticleÂ
CASÂ
Google ScholarÂ
Hou, X., Liu, H. & Huang, H. Iron-catalyzed fluoroalkylative alkylsulfonylation of alkenes via radical-anion relay. Nat. Commun. 15, 1480 (2024).ArticleÂ
ADSÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Bernardi, F., Cherry, W., Shaik, S. & Epiotis, N. D. Structure of fluoromethyl radicals. Conjugative and inductive effects. J. Am. Chem. Soc. 100, 1352–1356 (1978).ArticleÂ
CASÂ
Google ScholarÂ
Parsaee, F. et al. Radical philicity and its role in selective organic transformations. Nat. Rev. Chem. 5, 486–499 (2021).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Schutter, C., Pfund, E. & Lequeux, T. Radical conjugate addition of ambiphilic fluorinated free radicals. Tetrahedron 69, 5920–5926 (2013).ArticleÂ
Google ScholarÂ
Cheng, X. et al. Organozinc pivalates for cobalt-catalyzed difluoroalkylarylation of alkenes. Nat. Commun. 12, 4366 (2021).ArticleÂ
ADSÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Lin, J. et al. Salt-stabilized alkylzinc pivalates: versatile reagents for cobalt-catalyzed selective 1,2-dialkylation. Chem. Sci. 14, 8672–8680 (2023).ArticleÂ
ADSÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Loven, R. & Speckamp, W. N. A novel 1,4-aryl radical rearrangement. Tetrahedron Lett. 13, 1567–1570 (1972).ArticleÂ
Google ScholarÂ
Monos, T. M., Mcatee, R. C. & Stephenson, C. R. J. Arylsulfonylacetamides as bifunctional reagents for alkene aminoarylation. Science 361, 1369–1373 (2018).ArticleÂ
ADSÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Noten, E. A., Ng, C. H., Wolesensky, R. M. & Stephenson, C. R. J. A general alkene aminoarylation enabled by N-centred radical reactivity of sulfinamides. Nat. Chem. 16, 599–606 (2024).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Hervieu, C. et al. Chiral arylsulfinylamides as reagents for visible light-mediated asymmetric alkene aminoarylations. Nat. Chem. 16, 607–614 (2024).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Yu, J., Wu, Z. & Zhu, C. Efficient docking–migration strategy for selective radical difluoromethylation of alkenes. Angew. Chem. Int. Ed. 57, 17156–17160 (2018).ArticleÂ
CASÂ
Google ScholarÂ
Wu, X. & Zhu, C. Radical-mediated remote functional group migration. Acc. Chem. Res. 53, 1620–1636 (2020).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Liu, J. et al. Polarity umpolung strategy for the radical alkylation of alkenes. Angew. Chem. Int. Ed. 59, 8195–8202 (2020).ArticleÂ
CASÂ
Google ScholarÂ
Abrams, R. & Clayden, J. Photocatalytic difunctionalization of vinyl ureas by radical addition polar Truce–Smiles rearrangement cascades. Angew. Chem. Int. Ed. 59, 11600–11606 (2020).ArticleÂ
CASÂ
Google ScholarÂ
Yan, J. et al. A radical smiles rearrangement promoted by neutral eosin Y as a direct hydrogen atom transfer photocatalyst. J. Am. Chem. Soc. 142, 11357–11362 (2020).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Hervieu, C. et al. Asymmetric, visible light-mediated radical sulfinyl-Smiles rearrangement to access all-carbon quaternary stereocentres. Nat. Chem. 13, 327–334 (2021).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Ni, C., Hu, M. & Hu, J. Good partnership between sulfur and fluorine: sulfur-based fluorination and fluoroalkylation reagents for organic synthesis. Chem. Rev. 115, 765–825 (2015).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Rong, J. et al. Radical fluoroalkylation of isocyanides with fluorinated sulfones by visible-light photoredox catalysis. Angew. Chem. Int. Ed. 55, 2743–2747 (2016).ArticleÂ
CASÂ
Google ScholarÂ
Wei, J. et al. Transition-metal-free electrophilic fluoroalkanesulfinylation of electron-rich (het)arenes with fluoroalkyl heteroaryl sulfones via C(Het)−S and S=O bond cleavage. Adv. Synth. Catal. 361, 5528–5533 (2019).ArticleÂ
CASÂ
Google ScholarÂ
Zhou, X., Ni, C., Deng, L. & Hu, J. Electrochemical reduction of fluoroalkyl sulfones for radical fluoroalkylation of alkenes. Chem. Commun. 57, 8750–8753 (2021).ArticleÂ
CASÂ
Google ScholarÂ
Pereira, M. & Vale, N. Saquinavir: From HIV to COVID-19 and cancer treatment. Biomolecules 12, 944 (2022).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Friestad, G. K. & Qin, J. Highly stereoselective intermolecular radical addition to aldehyde hydrazones from a chiral 3-amino-2-oxazolidinone. J. Am. Chem. Soc. 122, 8329–8330 (2000).ArticleÂ
CASÂ
Google ScholarÂ
Shen, Y. & Friestad, G. K. Comparison of electrophilic amination reagents for n-amination of 2-oxazolidinones and application to synthesis of chiral hydrazones. J. Org. Chem. 67, 6236–6239 (2002).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Han, B. et al. Photocatalytic enantioselective α-aminoalkylation of acyclic imine derivatives by a chiral copper catalyst. Nat. Commun. 10, 3804 (2019).ArticleÂ
ADSÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Du, Y.-D. et al. Organophotocatalysed synthesis of 2-piperidinones in one step via [1 + 2 + 3] strategy. Nat. Commun. 14, 5339 (2023).ArticleÂ
ADSÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Guo, H.-M. & Wu, X. Selective deoxygenative alkylation of alcohols via photocatalytic domino radical fragmentations. Nat. Commun. 12, 5365 (2021).ArticleÂ
ADSÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Bloom, S. et al. Decarboxylative alkylation for site-selective bioconjugation of native proteins via oxidation potentials. Nat. Chem. 10, 205–211 (2018).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Streuff, J. & Gansäuer, A. Metal-catalyzed β-functionalization of Michael acceptors through reductive radical addition reactions. Angew. Chem. Int. Ed. 54, 14232–14242 (2015).ArticleÂ
CASÂ
Google ScholarÂ
Jiang, H. & Studer, A. Iminyl-radicals by oxidation of α-imino-oxy acids: photoredox-neutral alkene carboimination for the synthesis of pyrrolines. Angew. Chem. Int. Ed. 56, 12273–12276 (2017).ArticleÂ
CASÂ
Google ScholarÂ
Jin, J. & Newcomb, M. Rate constants and Arrhenius functions for ring opening of a cyclobutylcarbinyl radical clock and for hydrogen atom transfer from the Et3B−MeOH complex. J. Org. Chem. 73, 4740–4742 (2008).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Shinkai, H., Maeda, K., Yamasaki, T., Okamoto, H. & Uchida, I. Bis(2-(Acylamino)phenyl) disulfides, 2-(Acylamino)benzenethiols, and S-(2-(acylamino)phenyl) alkanethioates as novel inhibitors of cholesteryl ester transfer protein. J. Med. Chem. 43, 3566–3572 (2000).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ