Metal-free Trifluoromethylation of Aromatic and Heteroaromatic Aldehydes and Ketones

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2014 Jul 9

PMID 25001876

Citations 10

Authors

Yupu Qiao

Tuda Si

Ming-Hsiu Yang

Ryan A Altman

Affiliations

Soon will be listed here.

Abstract

The ability to convert simple and common substrates into fluoroalkyl derivatives under mild conditions remains an important goal for medicinal and agricultural chemists. One representative example of a desirable transformation involves the conversion of aromatic and heteroaromatic ketones and aldehydes into aryl and heteroaryl β,β,β-trifluoroethylarenes and -heteroarenes. The traditional approach for this net transformation involves stoichiometric metals and/or multistep reaction sequences that consume excessive time, material, and labor resources while providing low yields of products. To complement these traditional strategies, we report a one-pot metal-free decarboxylative procedure for accessing β,β,β-trifluoroethylarenes and -heteroarenes from readily available ketones and aldehydes. This method features several benefits, including ease of operation, readily available reagents, mild reaction conditions, high functional-group compatibility, and scalability.

Citing Articles

Fluorine-Retentive Strategies for the Functionalization of -Difluoroalkenes.

Sorrentino J, Altman R Synthesis (Stuttg). 2021; 53(21):3935-3950.

PMID: 34707322 PMC: 8545266. DOI: 10.1055/a-1547-9270.

Cobalt-Catalyzed Selective Unsymmetrical Dioxidation of -Difluoroalkenes.

Orsi D, Douglas J, Sorrentino J, Altman R J Org Chem. 2020; 85(16):10451-10465.

PMID: 32697905 PMC: 7442739. DOI: 10.1021/acs.joc.0c00415.

Organocatalytic Strategy for Hydrophenolation of -Difluoroalkenes.

Orsi D, Yadav M, Altman R Tetrahedron. 2020; 75(32):4325-4336.

PMID: 32103843 PMC: 7043310. DOI: 10.1016/j.tet.2019.04.016.

Catalytic One-Step Deoxytrifluoromethylation of Alcohols.

de Azambuja F, Lovrien S, Ross P, Ambler B, Altman R J Org Chem. 2019; 84(4):2061-2071.

PMID: 30632749 PMC: 6387626. DOI: 10.1021/acs.joc.8b03072.

Base Catalysis Enables Access to α,α-Difluoroalkylthioethers.

Orsi D, Easley B, Lick A, Altman R Org Lett. 2017; 19(7):1570-1573.

PMID: 28332397 PMC: 5485667. DOI: 10.1021/acs.orglett.7b00386.

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