Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/metal-free-direct-aryltrifluoromethylation-of-allylic-alcohols-with-xzlsgPcsBy
References (63)
-
Hiromichi Egami, Mikiko Sodeoka (2014)
Trifluormethylierung von Alkenen unter gleichzeitiger Einführung weiterer funktioneller GruppenAngewandte Chemie, 126
-
Yu-Tao He, Lian‐Hua Li, Zhao-Zhao Zhou, Huiliang Hua, Yi-Feng Qiu, Xue-Yuan Liu, Yong‐Min Liang (2014)
Copper-catalyzed three-component cyanotrifluoromethylation/azidotrifluoromethylation and carbocyclization of 1,6-enynes.Organic letters, 16 15
-
Cai Zhang (2014)
Recent advances in trifluoromethylation of organic compounds using Umemoto's reagents.Organic & biomolecular chemistry, 12 34
-
Yusuke Yasu, Y. Arai, Ren Tomita, T. Koike, M. Akita (2014)
Highly regio- and diastereoselective synthesis of CF3-substituted lactones via photoredox-catalyzed carbolactonization of alkenoic acids.Organic letters, 16 3
-
Cheng‐Pan Zhang, Zong-Ling Wang, Qing‐Yun Chen, Chun-Tao Zhang, Yucheng Gu, Ji-Chang Xiao (2011)
Generation of the CF3 radical from trifluoromethylsulfonium triflate and its trifluoromethylation of styrenes.Chemical communications, 47 23
-
Wei Wei, Jiangwei Wen, Daoshan Yang, Xiaoxia Liu, Meng-Ping Guo, Ruimei Dong, Hua Wang (2014)
Metal-free direct trifluoromethylation of activated alkenes with Langlois' reagent leading to CF3-containing oxindoles.The Journal of organic chemistry, 79 9
-
S. Bonesi, M. Fagnoni (2010)
The aromatic carbon-carbon ipso-substitution reaction.Chemistry, 16 46
-
Tao Shen, Yizhi Yuan, Song Song, N. Jiao (2014)
Iron-catalyzed aerobic difunctionalization of alkenes: a highly efficient approach to construct oxindoles by C-S and C-C bond formation.Chemical communications, 50 31
-
Leiyang Lv, Shenglin Lu, Q. Guo, B. Shen, Zhiping Li (2015)
Iron-catalyzed acylation-oxygenation of terminal alkenes for the synthesis of dihydrofurans bearing a quaternary carbon.The Journal of organic chemistry, 80 1
-
A. Carboni, Guillaume Dagousset, Emmanuel Magnier, Géraldine Masson (2014)
Photoredox-induced three-component oxy-, amino-, and carbotrifluoromethylation of enecarbamates.Organic letters, 16 4
-
Eunjin Kim, Sungkyu Choi, Hee‐Yeon Kim, E. Cho (2013)
Generation of CF3-containing epoxides and aziridines by visible-light-driven trifluoromethylation of allylic alcohols and amines.Chemistry, 19 20
-
Pan Xu, Jin Xie, Qicai Xue, C. Pan, Yixiang Cheng, Chengjian Zhu (2013)
Visible-light-induced trifluoromethylation of N-aryl acrylamides: a convenient and effective method to synthesize CF(3)-containing oxindoles bearing a quaternary carbon center.Chemistry, 19 42
-
Ashutosh Singh, Ruchi Chawla, Twinkle Keshari, Vinod Yadav, L. Yadav (2014)
Aerobic oxysulfonylation of alkenes using thiophenols: an efficient one-pot route to β-ketosulfones.Organic & biomolecular chemistry, 12 42
-
Tianfei Liu, Q. Shen (2012)
Progress in Copper‐Mediated Formation of Trifluoromethylated ArenesEuropean Journal of Organic Chemistry, 2012
-
Ren Tomita, Yusuke Yasu, T. Koike, M. Akita (2014)
Combining photoredox-catalyzed trifluoromethylation and oxidation with DMSO: facile synthesis of α-trifluoromethylated ketones from aromatic alkenes.Angewandte Chemie, 53 28
-
M. Schneider (1986)
2-Alkyl-substituted 1,1-bis(4-acetoxyphenyl)-2-phenylethenes. Estrogen receptor affinity, estrogenic and antiestrogenic properties, and mammary tumor inhibiting activity.Journal of medicinal chemistry, 29 8
-
S. Buchwald, R. Zhu (2012)
Copper-Catalyzed Oxytrifluoromethylation of Unactivated Alkenes -
Sebastián Barata‐Vallejo, B. Lantaño, A. Postigo (2014)
Recent advances in trifluoromethylation reactions with electrophilic trifluoromethylating reagents.Chemistry, 20 51
-
T. Koike, M. Akita (2014)
Recent progress in transition-metal-catalyzed trifluoromethylation of olefins using electrophilic CF3 reagentsJournal of Fluorine Chemistry, 167
-
Twinkle Keshari, V. Yadav, V. Srivastava, L. Yadav (2014)
Visible light organophotoredox catalysis: a general approach to β-keto sulfoxidation of alkenesGreen Chemistry, 16
-
C. Rüchardt, R. Hecht (1965)
Radikalumlagerungen, VII: Relative Wanderungsgeschwindigkeiten substituierter Phenylreste beim thermischen Zerfall von β‐Aryl‐perisovaleriansäure‐tert.‐butylesternChemische Berichte, 98
-
Wangqing Kong, M. Casimiro, E. Merino, C. Nevado (2013)
Copper-catalyzed one-pot trifluoromethylation/aryl migration/desulfonylation and C(sp2)-N bond formation of conjugated tosyl amides.Journal of the American Chemical Society, 135 39
-
Masaki Shimizu, T. Hiyama (2005)
Moderne Synthesemethoden für fluorierte VerbindungenAngewandte Chemie, 117
-
Yu-Tao He, Lian‐Hua Li, Yan‐Fang Yang, Zhao-Zhao Zhou, Huiliang Hua, Xue-Yuan Liu, Yong‐Min Liang (2014)
Copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes.Organic letters, 16 1
-
E. Merino, C. Nevado (2014)
Addition of CF3 across unsaturated moieties: a powerful functionalization toolChemical Society Reviews, 43
-
Pin Gao, Yong-Wen Shen, R. Fang, X. Hao, Zi‐Hang Qiu, Fan Yang, Xiao-Biao Yan, Qiang Wang, Xiang Gong, Xue-Yuan Liu, Yong‐Min Liang (2014)
Copper-catalyzed one-pot trifluoromethylation/aryl migration/carbonyl formation with homopropargylic alcohols.Angewandte Chemie, 53 29
-
Fei Wang, Xiaoxu Qi, Z. Liang, Pinhong Chen, Guosheng Liu (2014)
Copper-catalyzed intermolecular trifluoromethylazidation of alkenes: convenient access to CF3 -containing alkyl azides.Angewandte Chemie, 53 7
-
Qingquan Lu, Chao Liu, Zhiyuan Huang, Yiyang Ma, Jian Zhang, A. Lei (2014)
Relay cooperation of K2S2O8 and O2 in oxytrifluoromethylation of alkenes using CF3SO2Na.Chemical communications, 50 91
-
Hongwei Zhang, W. Pu, T. Xiong, Yan Li, Xuefeng Zhou, K. Sun, Qun Liu, Qian Zhang (2013)
Copper-catalyzed intermolecular aminocyanation and diamination of alkenes.Angewandte Chemie, 52 9
-
Xue-Qiang Chu, Huanxin Meng, Y. Zi, Xiao-Ping Xu, S. Ji (2014)
Metal-free oxidative radical addition of carbonyl compounds to α,α-diaryl allylic alcohols: synthesis of highly functionalized ketones.Chemistry, 20 51
-
V. Lubczyk, H. Bachmann, R. Gust (2002)
Investigations on estrogen receptor binding. The estrogenic, antiestrogenic, and cytotoxic properties of C2-alkyl-substituted 1,1-bis(4-hydroxyphenyl)-2-phenylethenes.Journal of medicinal chemistry, 45 24
-
Zhi‐Min Chen, Wei-Song Bai, Shao-Hua Wang, Bin Yang, Y. Tu, Fu‐Min Zhang (2013)
Copper-catalyzed tandem trifluoromethylation/semipinacol rearrangement of allylic alcohols.Angewandte Chemie, 52 37
-
H. Egami, R. Shimizu, Yoshihiko Usui, M. Sodeoka (2013)
Iron-catalyzed trifluoromethylation with concomitant C-C bond formation via 1,2-migration of an aryl group.Chemical communications, 49 66
-
A. Dilman, V. Levin (2011)
Nucleophilic Trifluoromethylation of C=N BondsEuropean Journal of Organic Chemistry, 2011
-
Yining Ji, Tobias Brueckl, R. Baxter, Yuta Fujiwara, I. Seiple, Shun Su, D. Blackmond, P. Baran (2011)
Innate C-H trifluoromethylation of heterocyclesProceedings of the National Academy of Sciences, 108
-
Wei Wei, Jiangwei Wen, Daoshan Yang, Huijun Jing, J. You, Hua Wang (2015)
Direct difunctionalization of alkynes with sulfinic acids and molecular iodine: a simple and convenient approach to (E)-β-iodovinyl sulfonesRSC Advances, 5
-
Wei Zhu, Jiang Wang, Shuni Wang, Zhanni Gu, J. Aceña, K. Izawa, Hong Liu, V. Soloshonok (2014)
Recent advances in the trifluoromethylation methodology and new CF3-containing drugsJournal of Fluorine Chemistry, 167
-
Xiaowu Liu, Fei Xiong, Xuanping Huang, Liang Xu, Pengfei Li, Xiaoxing Wu (2013)
Copper-catalyzed trifluoromethylation-initiated radical 1,2-aryl migration in α,α-diaryl allylic alcohols.Angewandte Chemie, 52 27
-
Yusuke Yasu, T. Koike, M. Akita (2012)
Three-component oxytrifluoromethylation of alkenes: highly efficient and regioselective difunctionalization of C=C bonds mediated by photoredox catalysts.Angewandte Chemie, 51 38
-
R. McDonald, Guosheng Liu, S. Stahl (2011)
Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.Chemical reviews, 111 4
-
Zhaojia Hang, Zejiang Li, Zhong-Quan Liu (2014)
Iodotrifluoromethylation of alkenes and alkynes with sodium trifluoromethanesulfinate and iodine pentoxide.Organic letters, 16 14
-
A. Carboni, Guillaume Dagousset, Emmanuel Magnier, G. Masson (2014)
One pot and selective intermolecular aryl- and heteroaryl-trifluoromethylation of alkenes by photoredox catalysis.Chemical communications, 50 91
-
Liping Zhu, Guoqiang Wang, Quanping Guo, Zhao-Qin Xu, Di Zhang, Rui Wang (2014)
Copper-catalyzed intramolecular oxytrifluoromethylthiolation of unactivated alkenes.Organic letters, 16 20
-
Fei Wang, Dinghai Wang, X. Mu, Pinhong Chen, Guosheng Liu (2014)
Copper-catalyzed intermolecular trifluoromethylarylation of alkenes: mutual activation of arylboronic acid and CF3+ reagent.Journal of the American Chemical Society, 136 29
-
W. Fu, Fen Xu, Yuqin Fu, Chen Xu, Shihui Li, Dapeng Zou (2014)
A Metal‐Free Route to CF3‐Containing Oxindoles by PhI(OAc)2‐Mediated Trifluoromethylation of N‐Arylacrylamides with TMSCF3European Journal of Organic Chemistry, 2014
-
Xingyu Jiang, F. Qing (2013)
Copper-catalyzed three-component oxytrifluoromethylation of alkenes with sodium trifluoromethanesulfinate and hydroxamic acid.Angewandte Chemie, 52 52
-
H. Egami, R. Shimizu, S. Kawamura, M. Sodeoka (2013)
Alkene trifluoromethylation coupled with C-C bond formation: construction of trifluoromethylated carbocycles and heterocycles.Angewandte Chemie, 52 14
-
T. Liang, Constanze Neumann, T. Ritter (2013)
Introduction of fluorine and fluorine-containing functional groups.Angewandte Chemie, 52 32
-
M. Tada, Kunimi Inoue, M. Okabe (1983)
Aryl rearrangement on the photolysis of 2-aryl-2-ethoxy-2-phenylethyl cobaloxime.Bulletin of the Chemical Society of Japan, 56
-
M. Shimizu, T. Hiyama (2004)
Modern synthetic methods for fluorine-substituted target molecules.Angewandte Chemie, 44 2
-
Theresa Liang, Constanze Neumann, Tobias Ritter (2013)
Einführung von Fluor und fluorhaltigen funktionellen GruppenAngewandte Chemie, 125
-
Sophie Purser, Peter Moore, S. Swallow, V. Gouverneur (2008)
Fluorine in medicinal chemistry.Chemical Society reviews, 37 2
-
Se Oh, Yashwardhan Malpani, Neul Ha, Young-Sik Jung, S. Han (2014)
Vicinal difunctionalization of alkenes: chlorotrifluoromethylation with CF3SO2Cl by photoredox catalysis.Organic letters, 16 5
-
Carla Antunes, M. Bietti, G. Ercolani, O. Lanzalunga, M. Salamone (2005)
The effect of ring substitution on the O-neophyl rearrangement of 1,1-diarylalkoxyl radicals. A product and time-resolved kinetic study.The Journal of organic chemistry, 70 10
-
Fang Yang, Piyatida Klumphu, Yongping Liang, B. Lipshutz (2014)
Copper-catalyzed trifluoromethylation of N-arylacrylamides "on water" at room temperature.Chemical communications, 50 8
-
Xiang Dong, Ruili Sang, Qiang Wang, Xiangying Tang, M. Shi (2013)
Copper-catalyzed trifluoromethylation and cyclization of aromatic-sulfonyl-group-tethered alkenes for the construction of 1,2-benzothiazinane dioxide type compounds.Chemistry, 19 50
-
Guillaume Dagousset, A. Carboni, Emmanuel Magnier, G. Masson (2014)
Photoredox-induced three-component azido- and aminotrifluoromethylation of alkenes.Organic letters, 16 16
-
A. Studer (2012)
Die “Renaissance” der radikalischen TrifluormethylierungAngewandte Chemie, 124
-
H. Egami, M. Sodeoka (2014)
Trifluoromethylation of alkenes with concomitant introduction of additional functional groups.Angewandte Chemie, 53 32
-
Xiao‐Feng Wu, H. Neumann, M. Beller (2012)
Recent developments on the trifluoromethylation of (hetero)arenes.Chemistry, an Asian journal, 7 8
-
Dengfu Lu, Cheng-Liang Zhu, Zhenhua Jia, Hao Xu (2014)
Iron(II)-Catalyzed Intermolecular Amino-Oxygenation of Olefins through the N–O Bond Cleavage of Functionalized HydroxylaminesJournal of the American Chemical Society, 136
-
A. Studer (2012)
A "Renaissance" in radical trifluoromethylation.Angewandte Chemie, 51 36
-
O. Tomashenko, V. Grushin (2011)
Aromatic trifluoromethylation with metal complexes.Chemical reviews, 111 8
- Publisher
- Wiley
- Copyright
- © 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
- ISSN
- 2193-5807
- eISSN
- 2193-5815
- DOI
- 10.1002/ajoc.201500096
- Publisher site
- See Article on Publisher Site
Abstract
A metal‐free and cost‐effective synthetic protocol for selective aryltrifluoromethylation of allylic alcohols with Langlois’ reagent (CF3SO2Na) through cascade trifluoromethyl radical addition/1,2‐aryl migration has been developed. The highlights of this procedure are operational simplicity, excellent functional group tolerance, and mild reaction conditions.
Journal
Asian Journal of Organic Chemistry – Wiley
Published: Jul 1, 2015
Keywords: ; ; ; ;