Chinese Journal of Applied Chemistry
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ZENG Wei, CHEN Fuxue*
Received:
2013-07-25
Revised:
2013-09-26
Published:
2014-06-10
Online:
2014-06-10
Contact:
fuxue chen
CLC Number:
ZENG Wei, CHEN Fuxue*. Recent Advances in Radical Trifluoromethylation Reactions[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.30378.
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[1] Müller K,Faeh C,Diederich F. Fluorine in Pharmaceuticals:Looking Beyond Intuition[J]. Science,2007,317:1881-1886.[2] Purser S,Moore P R,Gouverneur V,et al. Fluorine in Medicinal Chemistry[J]. Chem Soc Rev,2008,37:320-330.[3] QING Fengling. Recent Advances of Trifluoromethylation[J]. Chinese J Org Chem,2012,32:815-824(in Chinese).卿凤翎. 从三氟甲基化反应的近年进展看有机氟化学的发展趋势[J]. 有机化学,2012,32:815-824.[4] Michael B S,Jerry M. Advanced Organic Chemistry Part A:Structure and Mechanisms[M]. 4th Edition. NY 10013,USA:Springer Science+Business Media,LLC,2008. Chapter 11,982.[5] Kirsch P. Mordern Fluoroorganic Chemistry[M]. Wiley-VCH,2004.[6] Studer A. A “Renaissance” in Radical Trifluoromethylation[J]. Angew Chem Int Ed,2012,51:8950-8958.[7] WANG Xi,ZHANG Yan,WANG Jianbo. Recent Development of Trifluoromethylation through Trifluoromethyl Radical[J]. Sci Sin Chim,2012,42:1417-1427(in Chinese).王兮,张艳,王剑波. 经由三氟甲基自由基的三氟甲基化反应研究进展[J]. 中国科学:化学,2012,42:1417-1427.[8] Haszeldine R N. Reactions of Fluorocarbon Radicals:Ⅰ.The Reaction of Iodotrifluoromethane with Ethylene and Tetrafluoroethylene[J]. J Chem Soc,1949:2856-2861.[9] Maruoka K,Sano H,Yamamoto H,et al. Organoaluminum-Induced Addition of Polyhalomethane to Olefins[J]. Chem Lett,1985,14:1689-1692.[10] Miura K,Taniguchi M,Utimoto K,et al. Triethylborane Induced Perfluoroalkylation of Silyl Enol Ethers or Germyl Enol Ethers with Perfluoroalkyl Iodides[J]. Tetrahedron Lett,1990,31:6391-6394.[11] Yajima T,Nagano H,Saito C. Radical-mediated Hydroxytrifluoromethylation of α,β-Unsaturated Esters[J]. Tetrahedron Lett,2003,44:7027-7029.[12] Itoh Y,Mikami K. Facile Radical Trifluoromethylation of Lithium Enolates[J]. Org Lett,2005,7:4883-4885.[13] Itoh Y,Mikami K. Radical Trifluoromethylation of Ketone Li Enolates[J]. Tetrahedron,2006,62:7199-7203.[14] Wang Z,Lu X. Selective Ene-yne Coupling-Functionalization:A New Strategy in Constructing Heterocycles[J]. Tetrahedron,1995,51:2639-2658.[15] Petrik V,Cahard D. Radical Trifluoromethylation of Ammonium Enolates[J]. Tetrahedron Lett,2007,48:3327-3330.[16] Mikami K,Tomita Y,Itoh Y,et al. Radical Trifluoromethylation of Ketone Silyl Enol Ethers by Activation with Dialkylzinc[J]. Org Lett,2006,8:4671-4673.[17] Tomita Y,Itoh Y,Mikami K. Dialkylzinc-accelerated α-Trifluoromethylation of Carbonyl Compounds Catalyzed by Late-Transition-Metal Complexes[J]. Chem Lett,2008,37:1080-1081.[18] Ohtsuka Y,Uraguchi D,Yamakawa T,et al. Syntheses of 2-(Trifluoromethyl)-1,3-Dicarbonyl Compounds Through Direct Trifluoromethylation with CF3I and Their Application to Fluorinated Pyrazoles Syntheses[J]. Tetrahedron,2012,68:2636-2649.[19] Kino T,Nagase Y,Yamamoto K,et al. Trifluoromethylation of Various Aromatic Compounds by CF3I in the Presence of Fe(Ⅱ) Compound,H2O2 and Dimethylsulfoxide[J]. J Fluorine Chem,2010,131:98-105.[20] Nagib D A,Scott M E,MacMillan D W C. Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis[J]. J Am Chem Soc,2009,131:10875-10877.[21] Fuchikami T,Ojima I. Transition-metal Complex Catalyzed Polyfluoroalkylation:Ⅰ.Facile Addition of Polyfluoroalkyl Halides to Carbon-carbon Multiple Bonds[J]. Tetrahedron Lett,1984,25:303-306.[22] Ishihara T,Kuroboshi M,Okada Y. New Efficient Palladium-Catalyzed Perfluoroalkylation of Carbon-Carbon Multiple Bonds with F-Alkyl Iodides. An Expedient Route to F-alkylated Alkyl and Alkenyl Iodides[J]. Chem Lett,1986,15:1895-1896.[23] von Werner K. Reactions of Perfluoroalkyl Iodides with C-C-Multiple Bonds Induced by Transition Metal Centers[J]. J Fluorine Chem,1985,28:229-233.[24] Herrmann A T,Smith L L,Zakarian A. A Simple Method for Asymmetric Trifluoromethylation of N-Acyl Oxazolidinones via Ru-Catalyzed Radical Addition to Zirconium Enolates[J]. J Am Chem Soc,2012,134:6976-6979.[25] Ye Y,Sanford M S. Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in the Copper-Catalyzed Trifluoromethylation of Boronic Acids with CF3I[J]. J Am Chem Soc,2012,134:9034-9037.[26] Chen Q Y. Trifluoromethylation of Organic Halides with Difluorocarbene Precursors[J]. J Fluorine Chem,1995,72:241-246.[27] Roy S,Gregg B T,Roy S,et al. Trifluoromethylation of Aryl and Heteroaryl Halides[J]. Tetrahedron,2011,67:2161-2195.[28] Tomashenko O A,Grushin V V. Aromatic Trifluoromethylation with Metal Complexes[J]. Chem Rev,2011,111:4475-4521.[29] Kamigata N,Fukushima T,Sawada H,et al. Novel Perfluoroalkylation of Alkenes with Perfluoroalkanesulfonyl Chlorides Catalyzed by a Ruthenium(Ⅱ) Complex[J]. J Chem Soc Perkin Trans 1,1991:627-633.[30] Kamigata N,Fukushima T,Yoshida M,et al. Reactions of Perfluoroalkanesulfonyl Chlorides with Aromatic Compounds Catalyzed by a Ruthenium(Ⅱ) Complex[J]. Chem Lett,1990:649-650.[31] Kamigata N,Ohtsuka T,Shimizu T,et al. Direct Perfluoroalkylation of Aromatic and Heteroaromatic Compounds with Perfluoroalkanesulfonyl Chlorides Catalyzed by a Ruthenium(Ⅱ) Phosphine Complex[J]. J Chem Soc Perkin Trans 1,1994:1339-1346.[32] Nagib D A,MacMillan D W C. Trifluoromethylation of Arenes and Heteroarenes by Means of Photoredox Catalysis[J]. Nature,2011,480:224-228.[33] Langlois B R,Laurent E,Roidot N. Trifluoromethylation of Aromatic Compounds with Sodium Trifluoromethanesulfinate under Oxidative Conditions[J]. Tetrahedron Lett,1991,32:7525-7528.[34] Ji Y,Brueckl T,Baran P S,et al. Innate C-H Trifluoromethylation of Heterocycles[J]. Proc Natl Acad Sci USA,2011,108:14411-14415.[35] Billard T,Roques N,Langlois B R. Synthetic Uses of Thioesters of Trifluoromethylated Acids. Part 2:Reactions with Alkenes[J]. Tetrahedron Lett,2000,41:3069-3072.[36] Tanabe Y,Matsuo N,Ohno N. Direct Perfluoroalkylation including Trifluoromethylation of Aromatics with Perfluoro Carboxylic Acids Mediated by Xenon Difluoride[J]. J Org Chem,1988,53:4582-4585.[37] Sawada H,Nakayama M,Kamigata N,et al. Trifluoromethylation of Aromatic Compounds with Bis(trifluoroacetyl) Peroxide[J]. J Fluorine Chem,1990,46:423-431.[38] Lai C,Mallouk T E. A New Approach to the Photochemical Trifluoromethylation of Aromatic Compounds[J]. J Chem Soc Chem Commun,1993:1359-1361.[39] Prakash G K S,Yudin A K. Perfluoroalkylation with Organosilicon Reagents[J]. Chem Rev,1997,97:757-786.[40] Wu S,Zeng W,Chen F X,et al. Asymmetric Trifluoromethylation of Aromatic Aldehydes by Cooperative Catalysis with (IPr)CuF and Quinidine-Derived Quaternary Ammonium Salt[J]. Org Biomol Chem,2012,10:9334-9337.[41] Wu S,Guo J,Chen F X,et al. The Enantioselective Trifluoromethylation of Aromatic Aldehydes by Quaternary Ammonium Bromide and (IPr)CuF at Low Catalyst Loading[J]. J Fluorine Chem,2013,148:19-29.[42] Ye Y,Lee S H,Sanford M S. Silver-Mediated Trifluoromethylation of Arenes Using TMSCF3[J]. Org Lett,2011,13:5464-5467.[43] Zhang C P,Wang Z L,Xiao J C,et al. Generation of the CF3 Radical from Trifluoromethylsulfonium Triflate and Its Trifluoromethylation of Styrenes[J]. Chem Commun,2011,47:6632-6634.[44] Mizuta S,Verhoog S,Gouverneur V,et al. Catalytic Hydrotrifluoromethylation of Unactivated Alkenes[J]. J Am Chem Soc,2013,135:2505-2508.[45] Mizuta S,Engle K M,Gouverneur V,et al. Trifluoromethylation of Allylsilanes under Photoredox Catalysis[J]. Org Chem,2013,15:1250-1253.[46] Xu P,Xie J,Zhu C,et al. Visible-Light-Induced Trifluoromethylation of N-Aryl Acrylamides:A Convenient and Effective Method to Synthesize CF3-Containing Oxindoles Bearing a Quaternary Carbon Center[J]. Chem Eur J,2013,19:14039-14042.[47] Yasu Y,Koike T,Akita M. Intermolecular Aminotrifluoromethylation of Alkenes by Visible-Light-Driven Photoredox Catalysis[J]. Org Lett,2013,15:2136-2139.[48] Wang X,Zhang Y,Wang J B,et al. Copper-Catalyzed Direct C-H Trifluoromethylation of Quinones[J]. Org Lett,2013,15:3730-3733.[49] Liu X,Li P F,Wu X X,et al. Copper-Catalyzed Trifluoromethylation-Initiated Radical 1,2-Aryl Migration in α,α-Diaryl Allylic Alcohols[J]. Angew Chem Int Ed,2013,52:6962-6966.[50] Chen Z M,Tu Y Q,Zhang F M,et al. Copper-Catalyzed Tandem Trifluoromethylation/Semipinacol Rearrangement of Allylic Alcohols[J]. Angew Chem Int Ed,2013,52:9781-9785.[51] Kong W Q,Casimiro M,Nevado C,et al. Copper-Catalyzed One-Pot Trifluoromethylation/Aryl Migration/Desulfonylation and C(sp2)—N Bond Formation of Conjugated Tosyl Amides[J]. J Am Chem Soc,2013,135:14480-14483.[52] Gao P,Liu X Y,Liang Y M,et al. Copper-Catalyzed Trifluoromethylation Cyclization of Enynes:Highly Regioselective Construction of Trifluoromethylated Carbocycles and Heterocycles[J]. Chem Eur J,2013,19:14420-14424.[53] Yu Q,Ma S M. Copper-Catalyzed Cyclic Oxytrifluoromethylation of 2,3-Allenoic Acids to Trifluoromethylated Butenolides[J]. Chem Eur J,2013,19:13304-13308.[54] Dong X,Sang R,Shi M,et al. Copper-Catalyzed Trifluoromethylation and Cyclization of Aromatic-Sulfonyl-Group-Tethered Alkenes for the Construction of 1,2-Benzothiazinane Dioxide Type Compounds[J]. Chem Eur J,2013,19:16910-16915.[55] Okusu S,Sugita Y,Shibata N,et al. Regioselective 1,4-Trifluoromethylation of α,β-Unsaturated Ketones via a S-(trifluoromethyl)diphenylsulfonium Salts/copper System[J]. Beilstein J Org Chem,2013,9:2189-2193. |
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