The Experts below are selected from a list of 360 Experts worldwide ranked by ideXlab platform
Feng-ling Qing - One of the best experts on this subject based on the ideXlab platform.
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Silver-Mediated Oxidative Trifluoromethylation of Alcohols to Alkyl Trifluoromethyl Ethers.
Organic Letters, 2015Co-Authors: Xiu-hua Xu, Feng-ling QingAbstract:The development of an efficient and practical method for the preparation of alkyl trifluoromethyl ethers is urgently demanding. The silver-mediated oxidative O-Trifluoromethylation of primary, secondary, and tertiary alcohols with TMSCF3 under mild reaction conditions is established to provide a novel approach to a broad range of alkyl trifluoromethyl ethers. Further, this method is applied to the late-stage O-Trifluoromethylation of complex natural products and prescribed pharmaceutical agents.
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silver mediated oxidative Trifluoromethylation of phenols direct synthesis of aryl trifluoromethyl ethers
Angewandte Chemie, 2015Co-Authors: Jianbo Liu, Lingling Chu, Chao Chen, Zenghao Chen, Feng-ling QingAbstract:Aryl trifluoromethyl ethers (ArOCF3) are prevalent in pharmaceuticals, agrochemicals, and materials. However, methods for the general and efficient synthesis of these compounds are extremely underdeveloped and limited. Herein, we describe a highly efficient and general procedure for the direct O-Trifluoromethylation of unprotected phenols through a silver-mediated cross-coupling reaction using CF3SiMe3 as the CF3 source and exogenous oxidants. This novel oxidative Trifluoromethylation provides access to a wide range of aryl trifluoromethyl ethers from simple phenols. The mild process was also applied to the late-stage Trifluoromethylation of a medicinally relevant compound.
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oxidative Trifluoromethylation and trifluoromethylthiolation reactions using trifluoromethyl trimethylsilane as a nucleophilic cf3 source
ChemInform, 2014Co-Authors: Lingling Chu, Feng-ling QingAbstract:ConspectusThe trifluoromethyl group is widely prevalent in many pharmaceuticals and agrochemicals because its incorporation into drug candidates could enhance chemical and metabolic stability, improve lipophilicity and bioavailability, and increase the protein bind affinity. Consequently, extensive attention has been devoted toward the development of efficient and versatile methods for introducing the CF3 group into various organic molecules. Direct Trifluoromethylation reaction has become one of the most efficient and important approaches for constructing carbon–CF3 bonds. Traditionally, the nucleophilic Trifluoromethylation reaction involves an electrophile and the CF3 anion, while the electrophilic Trifluoromethylation reaction involves a nucleophile and the CF3 cation. In 2010, we proposed the concept of oxidative Trifluoromethylation: the reaction of nucleophilic substrates and nucleophilic Trifluoromethylation reagents in the presence of oxidants.In this Account, we describe our recent studies of ox...
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copper catalyzed oxidative Trifluoromethylation of terminal alkynes and aryl boronic acids using trifluoromethyl trimethylsilane
Journal of Organic Chemistry, 2012Co-Authors: Xueliang Jiang, Lingling Chu, Feng-ling QingAbstract:Trifluoromethylated acetylenes and arenes are widely applicable in the synthesis of pharmaceuticals and agrochemicals. In 2010, our group has reported the copper-mediated oxidative trifluomethylation of terminal alkynes and aryl boronic acids. This method allows a wide range of functional group tolerant trifluoromethylated acetylenes and arenes to be easily prepared. After the preliminary mechanistic studies of the oxidative Trifluoromethylation of terminal alkyne, an efficient copper-catalyzed oxidative Trifluoromethylation of terminal alkynes and aryl boronic acids has been developed. The catalytic protocol is successfully achieved by adding both the substrate and a portion of CF3TMS slowly using a syringe pump to the reaction mixture.
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copper catalyzed direct c h oxidative Trifluoromethylation of heteroarenes
Journal of the American Chemical Society, 2012Co-Authors: Lingling Chu, Feng-ling QingAbstract:This article describes the copper-catalyzed oxidative Trifluoromethylation of heteroarenes and highly electron-deficient arenes with CF3SiMe3 through direct C–H activation. In the presence of catalyst Cu(OAc)2, ligand 1,10-phenanthroline and cobases tert-BuONa/NaOAc, oxidative Trifluoromethylation of 1,3,4-oxadiazoles with CF3SiMe3 proceeded smoothly using either air or di-tert-butyl peroxide as an oxidant to give the corresponding trifluoromethylated 1,3,4-oxadiazoles in high yields. Di-tert-butyl peroxide was chosen as the suitable oxidant for oxidative Trifluoromethylation of 1,3-azoles and perfluoroarenes. Cu(OH)2 and Ag2CO3 were the best catalyst and oxidant for direct oxidative trifluoromethyaltion of indoles. The optimum reaction conditions enable oxidative Trifluoromethylation of a range of heteroarenes that bear numerous functional groups. The prepared trifluoromethylated heteroarenes are of importance in the areas of pharmaceuticals and agrochemicals. The preliminary mechanistic studies of these...
Jianbo Wang - One of the best experts on this subject based on the ideXlab platform.
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conversion of aromatic amino into trifluoromethyl groups through a sandmeyer type transformation
Synthesis, 2014Co-Authors: Xi Wang, Yan Zhang, Yujing Zhou, Jianbo WangAbstract:A novel strategy for aromatic Trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by Trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are smoothly converted under mild conditions.
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synthesis of 3 trifluoromethylpyrazoles via Trifluoromethylation cyclization of α β alkynic hydrazones using a hypervalent iodine reagent
Chemical Communications, 2014Co-Authors: Xi Wang, Songnan Zhang, Yan Zhang, Jianbo WangAbstract:A mild and efficient method for the synthesis of 3-trifluoromethylpyrazoles has been established via Trifluoromethylation/cyclization of α,β-alkynic hydrazones using a hypervalent iodine reagent under transition-metal-free conditions.
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silver mediated Trifluoromethylation of aryldiazonium salts conversion of amino group into trifluoromethyl group
Journal of the American Chemical Society, 2013Co-Authors: Xi Wang, Guojing Ji, Jiajie Feng, Songnan Zhang, Yuxuan Ye, Fanyang Mo, Yan Xu, Yan Zhang, Jianbo WangAbstract:A novel strategy for aromatic Trifluoromethylation by converting aromatic amino group into CF3 group is reported herein. This method, which can be considered as Trifluoromethylation variation of the classic Sandmeyer reaction, uses readily available aromatic amines as starting materials and is performed under mild conditions.
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copper catalyzed direct c h Trifluoromethylation of quinones
Organic Letters, 2013Co-Authors: Xi Wang, Jiajie Feng, Songnan Zhang, Yan Zhang, Jianbo WangAbstract:An efficient and practical methodology has been developed to introduce the CF3 group onto quinones through Cu(I)-catalyzed direct C–H Trifluoromethylation of quinones.
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copper catalyzed c sp3 c sp3 bond formation using a hypervalent iodine reagent an efficient allylic Trifluoromethylation
Journal of the American Chemical Society, 2011Co-Authors: Xi Wang, Jiajie Feng, Songnan Zhang, Yan Zhang, Jianbo WangAbstract:An efficient copper-catalyzed allylic Trifluoromethylation reaction has been developed. This reaction provides a general and straightforward way to synthesize allylic trifluoromethylated compounds under mild conditions.
Xi Wang - One of the best experts on this subject based on the ideXlab platform.
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conversion of aromatic amino into trifluoromethyl groups through a sandmeyer type transformation
Synthesis, 2014Co-Authors: Xi Wang, Yan Zhang, Yujing Zhou, Jianbo WangAbstract:A novel strategy for aromatic Trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by Trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are smoothly converted under mild conditions.
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synthesis of 3 trifluoromethylpyrazoles via Trifluoromethylation cyclization of α β alkynic hydrazones using a hypervalent iodine reagent
Chemical Communications, 2014Co-Authors: Xi Wang, Songnan Zhang, Yan Zhang, Jianbo WangAbstract:A mild and efficient method for the synthesis of 3-trifluoromethylpyrazoles has been established via Trifluoromethylation/cyclization of α,β-alkynic hydrazones using a hypervalent iodine reagent under transition-metal-free conditions.
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Conversion of Aromatic Amino into Trifluoromethyl Groups through a Sandmeyer-Type Transformation
synthesis stuttgart, 2014Co-Authors: Xi Wang, Xu Yan, Zhou Yujing, Zhang Yan, Wang JianboAbstract:A novel strategy for aromatic Trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by Trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are smoothly converted under mild conditions.http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000340875300004&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=8e1609b174ce4e31116a60747a720701Chemistry, OrganicSCI(E)4ARTICLEwangjb@pku.edu.cn162143-21484
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silver mediated Trifluoromethylation of aryldiazonium salts conversion of amino group into trifluoromethyl group
Journal of the American Chemical Society, 2013Co-Authors: Xi Wang, Guojing Ji, Jiajie Feng, Songnan Zhang, Yuxuan Ye, Fanyang Mo, Yan Xu, Yan Zhang, Jianbo WangAbstract:A novel strategy for aromatic Trifluoromethylation by converting aromatic amino group into CF3 group is reported herein. This method, which can be considered as Trifluoromethylation variation of the classic Sandmeyer reaction, uses readily available aromatic amines as starting materials and is performed under mild conditions.
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copper catalyzed direct c h Trifluoromethylation of quinones
Organic Letters, 2013Co-Authors: Xi Wang, Jiajie Feng, Songnan Zhang, Yan Zhang, Jianbo WangAbstract:An efficient and practical methodology has been developed to introduce the CF3 group onto quinones through Cu(I)-catalyzed direct C–H Trifluoromethylation of quinones.
Yan Zhang - One of the best experts on this subject based on the ideXlab platform.
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conversion of aromatic amino into trifluoromethyl groups through a sandmeyer type transformation
Synthesis, 2014Co-Authors: Xi Wang, Yan Zhang, Yujing Zhou, Jianbo WangAbstract:A novel strategy for aromatic Trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by Trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are smoothly converted under mild conditions.
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synthesis of 3 trifluoromethylpyrazoles via Trifluoromethylation cyclization of α β alkynic hydrazones using a hypervalent iodine reagent
Chemical Communications, 2014Co-Authors: Xi Wang, Songnan Zhang, Yan Zhang, Jianbo WangAbstract:A mild and efficient method for the synthesis of 3-trifluoromethylpyrazoles has been established via Trifluoromethylation/cyclization of α,β-alkynic hydrazones using a hypervalent iodine reagent under transition-metal-free conditions.
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silver mediated Trifluoromethylation of aryldiazonium salts conversion of amino group into trifluoromethyl group
Journal of the American Chemical Society, 2013Co-Authors: Xi Wang, Guojing Ji, Jiajie Feng, Songnan Zhang, Yuxuan Ye, Fanyang Mo, Yan Xu, Yan Zhang, Jianbo WangAbstract:A novel strategy for aromatic Trifluoromethylation by converting aromatic amino group into CF3 group is reported herein. This method, which can be considered as Trifluoromethylation variation of the classic Sandmeyer reaction, uses readily available aromatic amines as starting materials and is performed under mild conditions.
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copper catalyzed direct c h Trifluoromethylation of quinones
Organic Letters, 2013Co-Authors: Xi Wang, Jiajie Feng, Songnan Zhang, Yan Zhang, Jianbo WangAbstract:An efficient and practical methodology has been developed to introduce the CF3 group onto quinones through Cu(I)-catalyzed direct C–H Trifluoromethylation of quinones.
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copper catalyzed c sp3 c sp3 bond formation using a hypervalent iodine reagent an efficient allylic Trifluoromethylation
Journal of the American Chemical Society, 2011Co-Authors: Xi Wang, Jiajie Feng, Songnan Zhang, Yan Zhang, Jianbo WangAbstract:An efficient copper-catalyzed allylic Trifluoromethylation reaction has been developed. This reaction provides a general and straightforward way to synthesize allylic trifluoromethylated compounds under mild conditions.
Qilong Shen - One of the best experts on this subject based on the ideXlab platform.
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trifluoromethyl substituted sulfonium ylide rh catalyzed carbenoid addition to trifluoromethylthioether
Organic Letters, 2015Co-Authors: Yafei Liu, Xinxin Shao, Panpan Zhang, Qilong ShenAbstract:A highly efficient Rh-catalyzed carbenoid addition to trifluoromethylthioether for the formation of trifluoromethyl-substituted sulfonium ylide is described. The trifluoromethyl-substituted sulfonium ylide can act as an electrophilic Trifluoromethylation reagent, as demonstrated by Trifluoromethylation of β-ketoesters and aryl iodides.
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highly selective Trifluoromethylation of 1 3 disubstituted arenes through iridium catalyzed arene borylation
ChemInform, 2012Co-Authors: Tianfei Liu, Xinxin Shao, Qilong ShenAbstract:The sequential iridium-catalyzed borylation and copper-catalyzed Trifluoromethylation of arenes is performed under mild conditions and tolerates a variety of functional groups.
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highly selective Trifluoromethylation of 1 3 disubstituted arenes through iridium catalyzed arene borylation
Angewandte Chemie, 2012Co-Authors: Tianfei Liu, Xinxin Shao, Qilong ShenAbstract:The old one two: A sequential iridium-catalyzed borylation and copper-catalyzed Trifluoromethylation of arenes is described (see scheme; Pin = pinacol). The reaction is conducted under mild reaction conditions and tolerates a variety of functional groups. The advantages of this tandem procedure are demonstrated by the late-stage Trifluoromethylation of a number of biologically active molecules.
