Literature DB >> 23344691

A sterically demanding organo-superbase avoids decomposition of a naked trifluoromethyl carbanion directly generated from fluoroform.

Hiroyuki Kawai1, Zhe Yuan, Etsuko Tokunaga, Norio Shibata.   

Abstract

A simple strategy avoiding the decomposition of a naked trifluoromethyl anion to difluorocarbene by a sterically very demanding organo-superbase without the help of a trifluoromethyl anion reservoir such as DMF is reported. The direct non-metallic trifluoromethylation of carbonyl compounds using fluoroform in the presence of t-Bu-P4 base afforded trifluoromethyl alcohols in high yields.

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Year:  2013        PMID: 23344691     DOI: 10.1039/c3ob27368g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  11 in total

Review 1.  Repurposing of F-gases: challenges and opportunities in fluorine chemistry.

Authors:  Daniel J Sheldon; Mark R Crimmin
Journal:  Chem Soc Rev       Date:  2022-06-20       Impact factor: 60.615

2.  [11 C]Fluoroform, a Breakthrough for Versatile Labeling of PET Radiotracer Trifluoromethyl Groups in High Molar Activity.

Authors:  Mohammad B Haskali; Victor W Pike
Journal:  Chemistry       Date:  2017-05-17       Impact factor: 5.236

3.  Regioselective 1,4-trifluoromethylation of α,β-unsaturated ketones via a S-(trifluoromethyl)diphenylsulfonium salts/copper system.

Authors:  Satoshi Okusu; Yutaka Sugita; Etsuko Tokunaga; Norio Shibata
Journal:  Beilstein J Org Chem       Date:  2013-10-23       Impact factor: 2.883

4.  Direct nucleophilic trifluoromethylation of carbonyl compounds by potent greenhouse gas, fluoroform: Improving the reactivity of anionoid trifluoromethyl species in glymes.

Authors:  Takuya Saito; Jiandong Wang; Etsuko Tokunaga; Seiji Tsuzuki; Norio Shibata
Journal:  Sci Rep       Date:  2018-07-31       Impact factor: 4.379

5.  Cs₂CO₃-Initiated Trifluoro-Methylation of Chalcones and Ketones for Practical Synthesis of Trifluoromethylated Tertiary Silyl Ethers.

Authors:  Cheng Dong; Xing-Feng Bai; Ji-Yuan Lv; Yu-Ming Cui; Jian Cao; Zhan-Jiang Zheng; Li-Wen Xu
Journal:  Molecules       Date:  2017-05-18       Impact factor: 4.411

6.  Gas/Liquid-Phase Micro-Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N-Sulfinylimines.

Authors:  Kazuki Hirano; Satoshi Gondo; Nagender Punna; Etsuko Tokunaga; Norio Shibata
Journal:  ChemistryOpen       Date:  2019-02-05       Impact factor: 2.911

7.  A Gas Phase Route to [18F]fluoroform with Limited Molar Activity Dilution.

Authors:  Bo Yeun Yang; Sanjay Telu; Mohammad B Haskali; Cheryl L Morse; Victor W Pike
Journal:  Sci Rep       Date:  2019-10-16       Impact factor: 4.379

8.  Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system.

Authors:  Yamato Fujihira; Yumeng Liang; Makoto Ono; Kazuki Hirano; Takumi Kagawa; Norio Shibata
Journal:  Beilstein J Org Chem       Date:  2021-02-12       Impact factor: 2.883

9.  Organocatalyzed Trifluoromethylation of Ketones and Sulfonyl Fluorides by Fluoroform under a Superbase System.

Authors:  Satoshi Okusu; Kazuki Hirano; Etsuko Tokunaga; Norio Shibata
Journal:  ChemistryOpen       Date:  2015-08-06       Impact factor: 2.911

10.  Generation and Applications of the Hydroxide Trihydrate Anion, [OH(OH2 )3 ]- , Stabilized by a Weakly Coordinating Cation.

Authors:  Robin F Weitkamp; Beate Neumann; Hans-Georg Stammler; Berthold Hoge
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-09       Impact factor: 15.336

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