Literature DB >> 23425346

Nucleophilic trifluoromethylation of carbonyl compounds: trifluoroacetaldehyde hydrate as a trifluoromethyl source.

G K Surya Prakash1, Zhe Zhang, Fang Wang, Socrates Munoz, George A Olah.   

Abstract

A feasible nucleophilic trifluoromethylating protocol has been developed using trifluoroacetaldehyde hydrate as an atom-economical trifluoromethyl source. The reaction was found to be applicable to the nucleophilic trifluoromethylation of a broad spectrum of carbonyl compounds with satisfactory yields in general. DFT calculations have been performed to provide mechanistic insight into the present and related reactions employing 2,2,2-trifluoro-1-methoxyethanol and hexafluoroacetone hydrate.

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Year:  2013        PMID： 23425346      PMCID： PMC3675896          DOI： 10.1021/jo400202w

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  11 in total

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4.  Nucleophilic trifluoromethylation using trifluoromethyl iodide. A new and simple alternative for the trifluoromethylation of aldehydes and ketones.

Authors:  S Aït-Mohand; N Takechi; M Médebielle; W R Dolbier
Journal:  Org Lett       Date:  2001-12-27       Impact factor: 6.005

5.  Nucleophilic trifluoromethylation of carbonyl compounds and disulfides with trifluoromethane and silicon-containing bases

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Journal:  J Org Chem       Date:  2000-12-29       Impact factor: 4.354

6.  New stable reagents for the nucleophilic trifluoromethylation. 1. Trifluoromethylation Of carbonyl compounds with N-formylmorpholine derivatives

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Journal:  Org Lett       Date:  2000-07-13       Impact factor: 6.005

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8.  Taming of fluoroform: direct nucleophilic trifluoromethylation of Si, B, S, and C centers.

Authors:  G K Surya Prakash; Parag V Jog; Patrice T D Batamack; George A Olah
Journal:  Science       Date:  2012-12-07       Impact factor: 47.728

9.  Amidinate salt of hexafluoroacetone hydrate for the preparation of fluorinated compounds by the release of trifluoroacetate.

Authors:  Mark V Riofski; Allison D Hart; David A Colby
Journal:  Org Lett       Date:  2012-12-14       Impact factor: 6.005

10.  Alkoxide- and hydroxide-induced nucleophilic trifluoromethylation using trifluoromethyl sulfone or sulfoxide.

Authors:  G K Surya Prakash; Jinbo Hu; George A Olah
Journal:  Org Lett       Date:  2003-09-04       Impact factor: 6.005
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  3 in total

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Journal:  Chem       Date:  2016-09-08       Impact factor: 22.804

2.  Fluorine-decoupled carbon spectroscopy for the determination of configuration at fully substituted, trifluoromethyl- and perfluoroalkyl-bearing carbons: comparison with 19F-1H heteronuclear Overhauser effect spectroscopy.

Authors:  Appi Reddy Mandhapati; Takayuki Kato; Takahiko Matsushita; Bashar Ksebati; Andrea Vasella; Erik C Böttger; David Crich
Journal:  J Org Chem       Date:  2015-01-20       Impact factor: 4.354

3.  Synthesis of Ethers via Reaction of Carbanions and Monoperoxyacetals.

Authors:  ShivaKumar Kyasa; Rebecca N Meier; Ruth A Pardini; Tristan K Truttmann; Keith T Kuwata; Patrick H Dussault
Journal:  J Org Chem       Date:  2015-12-07       Impact factor: 4.354
  3 in total

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