- 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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- 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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- 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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- 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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