Organic Letters

, volume 19 , issue 19 , pages 5304-5307

Difluoromethylation of Carboxylic Acids via the Addition of Difluorinated Phosphorus Ylide to Acyl Chlorides

Alexey L Trifonov ^{1, 2}

Vitalij V Levin ¹

Marina I. Struchkova ¹

Alexander D Dilman ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation |

D. Mendeleev University of Chemical Technology of Russia, Higher Chemical College, Miusskaya sq. 9, 125047 Moscow, Russian Federation |

Publication type: Journal Article

Publication date: 2017-09-15

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.7b02601

Copy DOI

PubMed ID: 28915059

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

A one-step protocol for the difluoromethylation of carboxylic acids is described. The reaction involves the interaction of intermediate acyl chlorides with in situ generated difluorinated phosphorus ylide Ph3P═CF2. Aromatic acids can be selectively transformed within one step either to bis-difluoromethylated alcohols or to difluorinated ketones depending on the particular reaction conditions. For bulky α-branched carboxylic acids, only ketones are produced.

Found

11 citations

Dilman Alexander

DSc in Chemistry, associate member of the Russian Academy of Sciences

208 publications, 5 167 citations, 152 reviews

h-index: 39

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Organic Chemistry

1 citation

Prima Darya

🥼 🤝

PhD in Chemistry

21 publications, 412 citations

h-index: 9

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Heterocyclic compounds

Organic Chemistry

Organic synthesis

Organometallic Chemistry

Perfluorinated compounds

1 citation

Osipov Sergey

DSc in Chemistry

138 publications, 2 751 citations, 3 reviews

h-index: 29

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

1 citation

Sosnovskikh Vyacheslav

DSc in Chemistry, professor

355 publications, 4 743 citations

h-index: 30

Ural Federal University

1 citation

Morozova Sofia

🥼

PhD in Chemistry

46 publications, 1 084 citations, 131 reviews

h-index: 17

Moscow Institute of Physics and Technology

1 citation

Shchegolkov Evgeny

70 publications, 927 citations, 57 reviews

h-index: 16

Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Research interests

Organic synthesis

1 citation

Danshina Anastasia

🤝

26 publications, 98 citations

h-index: 6

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Moscow Institute of Physics and Technology

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Trifonov A. L. et al. Difluoromethylation of Carboxylic Acids via the Addition of Difluorinated Phosphorus Ylide to Acyl Chlorides // Organic Letters. 2017. Vol. 19. No. 19. pp. 5304-5307.

GOST all authors (up to 50) Copy

Trifonov A. L., Levin V. V., Struchkova M. I., Dilman A. D. Difluoromethylation of Carboxylic Acids via the Addition of Difluorinated Phosphorus Ylide to Acyl Chlorides // Organic Letters. 2017. Vol. 19. No. 19. pp. 5304-5307.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.7b02601

UR - https://doi.org/10.1021/acs.orglett.7b02601

TI - Difluoromethylation of Carboxylic Acids via the Addition of Difluorinated Phosphorus Ylide to Acyl Chlorides

T2 - Organic Letters

AU - Trifonov, Alexey L

AU - Levin, Vitalij V

AU - Struchkova, Marina I.

AU - Dilman, Alexander D

PY - 2017

DA - 2017/09/15

PB - American Chemical Society (ACS)

SP - 5304-5307

IS - 19

VL - 19

PMID - 28915059

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2017_Trifonov,

author = {Alexey L Trifonov and Vitalij V Levin and Marina I. Struchkova and Alexander D Dilman},

title = {Difluoromethylation of Carboxylic Acids via the Addition of Difluorinated Phosphorus Ylide to Acyl Chlorides},

journal = {Organic Letters},

year = {2017},

volume = {19},

publisher = {American Chemical Society (ACS)},

month = {sep},

url = {https://doi.org/10.1021/acs.orglett.7b02601},

number = {19},

pages = {5304--5307},

doi = {10.1021/acs.orglett.7b02601}

}

MLA

Cite this

MLA Copy

Trifonov, Alexey L., et al. “Difluoromethylation of Carboxylic Acids via the Addition of Difluorinated Phosphorus Ylide to Acyl Chlorides.” Organic Letters, vol. 19, no. 19, Sep. 2017, pp. 5304-5307. https://doi.org/10.1021/acs.orglett.7b02601.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)

Profiles

Alexander D Dilman