Literature DB >> 24555707

Catalytic C-H α-trifluoromethylation of α,β-unsaturated carbonyl compounds.

Zhongxue Fang1, Yongquan Ning, Pengbing Mi, Peiqiu Liao, Xihe Bi.   

Abstract

A copper(I)-catalyzed, regioselective C-H α-trifluoromethylation of α,β-unsaturated carbonyl compounds using Togni's reagent was developed. Diverse substrates, including enones as well as α,β-unsaturated esters, thioesters, and amides, stereospecifically afforded the corresponding (E)-α-trifluoromethylated products in moderate to high yields. Further, this method was applied to the C-H trifluoromethylation of drugs.

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Year:  2014        PMID: 24555707     DOI: 10.1021/ol5004498

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  Metal-Free Aminohalogenation of Quinones With Alkylamines and NXS at Room Temperature.

Authors:  Jia Li; Yu-An Li; Ge Wu; Xu Zhang
Journal:  Front Chem       Date:  2022-05-20       Impact factor: 5.545

Review 2.  Recent advances in direct trifluoromethylation of olefinic C-H bonds.

Authors:  Cao Yang; Akbar Hassanpour; Khatereh Ghorbanpour; Shahrzad Abdolmohammadi; Esmail Vessally
Journal:  RSC Adv       Date:  2019-09-03       Impact factor: 4.036

3.  Product Control in Alkene Trifluoromethylation: Hydrotrifluoromethylation, Vinylic Trifluoromethylation, and Iodotrifluoromethylation using Togni Reagent.

Authors:  Hiromichi Egami; Yoshihiko Usui; Shintaro Kawamura; Sayoko Nagashima; Mikiko Sodeoka
Journal:  Chem Asian J       Date:  2015-06-16

4.  Radiosynthesis of the anticancer nucleoside analogue Trifluridine using an automated 18F-trifluoromethylation procedure.

Authors:  Alice King; Andreas Doepner; David Turton; Daniela M Ciobota; Chiara Da Pieve; Anne-Christine Wong Te Fong; Gabriela Kramer-Marek; Yuen-Li Chung; Graham Smith
Journal:  Org Biomol Chem       Date:  2018-04-25       Impact factor: 3.876

5.  Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination.

Authors:  Jiyun Sun; Xiaohua Zhen; Huaibin Ge; Guangtao Zhang; Xuechan An; Yunfei Du
Journal:  Beilstein J Org Chem       Date:  2018-06-15       Impact factor: 2.883

6.  Metal-Free Vinyl C-H Sulfenylation/Alkyl Thiolation of Ketene Dithioacetals for the Synthesis of Polythiolated Alkenes.

Authors:  Leiling Deng; Yunyun Liu
Journal:  ACS Omega       Date:  2018-09-25

Review 7.  Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups.

Authors:  Xiaowei Li; Xiaolin Shi; Xiangqian Li; Dayong Shi
Journal:  Beilstein J Org Chem       Date:  2019-09-23       Impact factor: 2.883

8.  α-Trifluoromethyl Chalcones as Potent Anticancer Agents for Androgen Receptor-Independent Prostate Cancer.

Authors:  Yohei Saito; Atsushi Mizokami; Kouji Izumi; Renato Naito; Masuo Goto; Kyoko Nakagawa-Goto
Journal:  Molecules       Date:  2021-05-10       Impact factor: 4.411

  8 in total

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