- Electrochemical Synthesis Strategy for Cvinyl-CF3 Compounds through Decarboxylative Trifluoromethylation
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An efficient decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids using the Langlois reagent as a trifluoromethyl precursor has been achieved by an electro-oxidative strategy. Under catalyst-free and external oxidant-free electrolysis
- Hong, Huanliang,Li, Yibiao,Chen, Lu,Li, Bin,Zhu, Zhongzhi,Chen, Xiuwen,Chen, Ling,Huang, Yubing
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p. 5980 - 5986
(2019/05/10)
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- Electrochemical Decarboxylative Trifluoromethylation of α, β-Unsaturated Carboxylic Acids with CF3SO2Na
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A new method for the synthesis of vinyl trifluoromethyl compounds from α, β-unsaturated carboxylic acids and CF3SO2Na has been developed. This electrochemical decarboxylative trifluoro-methylation was found to be highly stereoselective and afforded products in good yields with wide substrate scope under metal-free and external chemical oxidant-free conditions.
- Li, Fang-Yuan,Lin, Dian-Zhao,He, Tian-Jun,Zhong, Wei-Qiang,Huang, Jing-Mei
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p. 2350 - 2354
(2019/04/13)
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- Phosphine-Relayed Aldehyde-Olefination and Aza-Wittig Reaction with 2,2,2-Trifluorodiazoethane
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Phosphine-relayed olefination and aza-Wittig reactions of readily available aldehydes with 2,2,2-trifluorodiazoethane (CF3CHN2) have been realized. This protocol enables the facile construction of a series of trifluoromethylated alkenes and hydrazones in good to high yield under mild conditions.
- Zhang, Fa-Guang,Lv, Ning,Zheng, Yan,Ma, Jun-An
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p. 723 - 730
(2018/07/29)
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- Domino Hydroboration/Trifluoromethylation of Alkynes Using Fluoroform-Derived [CuCF3]
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A domino hydroboration/trifluoromethylation (formal hydrotrifluoromethylation) of alkynes using the fluoroform-derived [CuCF3] reagent is achieved. Synthetically useful (E)-alkenyl-CF3 building blocks and 1,1-bis(trifluoromethyl)-substituted alkenes can be prepared under ambient conditions in one pot/one step from alkynes. The ultimate source of CF3 is the inexpensive industrial waste fluoroform.
- He, Lisi,Yang, Xinkan,Tsui, Gavin Chit
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p. 6192 - 6201
(2017/06/23)
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- Palladium-catalyzed geometrically selective hydrogenation of (Z)-trifluoromethyl alkenyl triflate: An efficient approach to (Z) or (E)-3,3,3-trifluoropropenyl derivatives
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A Pd-catalyzed hydrogenation of (Z)-trifluoromethyl alkenyl triflate providing either (Z)- or (E)-3,3,3-trifluoropropenyl derivatives with excellent divergent geometric control in good yield is described. Catalyzed by Pd(OAc)2/PPh3, the reduction of (Z)-trifluoromethyl alkenyl triflates with HSiEt3 gave (E)-3,3,3-trifluoropropenyl derivatives, and while using HCOOH/Et3N as the reducing agent, the (Z)-isomers were obtained through an elimination/hydrogenation tandem pathway. Both transformations showed excellent geometrical selectivity.
- Zhao, Yilong,Zhou, Yuhan,Zhang, Chunxia,Wang, Huan,Zhao, Jinfeng,Jin, Kun,Liu, Jihong,Liu, Jianhui,Qu, Jingping
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p. 5693 - 5700
(2017/07/22)
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- Metal-free radical trifluoromethylation of β-nitroalkenes through visible-light photoredox catalysis
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A catalytic method for functional group interconversion is immensely important in modern sciences. Here, we report an efficient catalytic conversion of nitroalkenes to highly stereoselective 1-trifluoromethylalkenes at room temperature. This unprecedented metal-free photocatalytic strategy is simple and operates under visible-light irradiation using the commercially available CF3 source.
- Midya, Siba P.,Rana, Jagannath,Abraham, Thomas,Aswin, Bhaskaran,Balaraman, Ekambaram
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p. 6760 - 6763
(2017/07/10)
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- An I2O5-promoted decarboxylative trifluoromethylation of cinnamic acids
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An I2O5-promoted decarboxylative trifluoromethylation of a series of cinnamic acids and their derivatives by using sodium trifluoromethanesulfinate in aqueous media was demonstrated. This strategy provides a safe and convenient access to various trifluoromethylated (E)-alkenes in a very high selectivity.
- Shang, Xiao-Jie,Li, Zejiang,Liu, Zhong-Quan
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supporting information
p. 233 - 235
(2015/02/02)
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- Decarboxylative and Denitrative Trifluoromethylation for the Synthesis of Cvinyl-CF3 Compounds with Togni (II) Reagent
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A highly efficient dimethylformamide (DMF)-promoted decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids with Togni (II) reagent under metal-free conditions has been developed. The reactions showed good yields, high stereoselectivities and excellent functional group tolerance. Mechanistic studies confirmed that free-radical processes were involved in this system since the CF3 radical had been clearly trapped by scavengers. This method has been extended to the denitrative trifluoromethylation of β-nitrostyrenes in the presence of an iron(III) catalyst.
- Ma, Jing-Jing,Yi, Wen-Bin,Lu, Guo-Ping,Cai, Chun
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supporting information
p. 3447 - 3452
(2016/01/25)
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- Copper-and iron-catalyzed decarboxylative tri-and difluoromethylation of α,β-unsaturated carboxylic acids with CF3SO2Na and (CF2HSO2)2Zn via a radical process
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A copper-catalyzed decarboxylative trifluoromethylation of various α,β-unsaturated carboxylic acids by using a stable and inexpensive solid, sodium trifluoromethanesulfinate (CF3SO2Na, Langlois reagent), was developed. In addition, an iron-catalyzed difluoromethylation of aryl-substituted acrylic acids by using zinc difluoromethanesulfinate (DFMS, (CF2HSO2)2Zn, Baran reagent) via a similar radical process was also achieved.
- Li, Zejiang,Cui, Zili,Liu, Zhong-Quan
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supporting information
p. 406 - 409
(2013/03/13)
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- Julia-Kocienski approach to trifluoromethyl-substituted alkenes
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A Julia-Kocienski approach to trifluoromethyl-substituted alkenes was evaluated in the reactions of 1,3-benzothiazol-2-yl, 1-phenyl-1H-tetrazol-5-yl, and 1-tbutyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfones with aldehydes. Among the various conditions tested, the best yields were obtained with 1-phenyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfone, in CsF-mediated, room temperature olefinations in DMSO. Aromatic aldehydes gave (trifluoromethyl)vinyl derivatives in 23-86% yields, with generally moderate stereoselectivity. Straightforward synthesis of the Julia-Kocienski reagent, and conversion to trifluoromethyl-substituted alkenes under mild reaction conditions, are the advantages of this approach.
- Ayeni, Deborah O.,Mandal, Samir K.,Zajc, Barbara
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supporting information
p. 6008 - 6011
(2013/10/22)
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- A domino approach of heck coupling for the synthesis of β-trifluoromethylstyrenes
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A domino approach of Heck coupling was used to synthesize β-trifluoromethylstyrene derivatives from iodoarenes and 1-iodo-3,3,3-trifluoropropane in moderate to good yields. This method avoids the use of low-boiling, gaseous reagents such as 3,3,3-trifluoropropene, and additives and phosphines in the catalytic system.
- Prakash, G. K. Surya,Krishnan, Hema S.,Jog, Parag V.,Iyer, Anjali P.,Olah, George A.
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supporting information; experimental part
p. 1146 - 1149
(2012/04/04)
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