Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products

David T. Smith; Edon Vitaku; Jon T. Njardarson

doi:10.1021/acs.orglett.7b01479

Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products

David T. Smith, Edon Vitaku, Jon T. Njardarson

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

A mild dearomatization enabled ortho-selective replacement of an aromatic C-H bond with a hexafluoroacetylacetone (hfacac) substituent has been developed. This reaction is dependent on a hypervalent iodine generated phenoxonium intermediate, a critical choice of solvent, and reagent addition order. The fluorinated dihydrobenzofuran product can be transformed into dihydrobenzofuran and benzofuran products decorated with a 2-trifluoromethyl group. The 3-trifluoromethylacyl substituted benzofurans rapidly form hydrates, which can be reduced to the corresponding alcohols.

Original language	English (US)
Pages (from-to)	3508-3511
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.7b01479
State	Published - Jul 7 2017
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.7b01479

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title = "Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products",

abstract = "A mild dearomatization enabled ortho-selective replacement of an aromatic C-H bond with a hexafluoroacetylacetone (hfacac) substituent has been developed. This reaction is dependent on a hypervalent iodine generated phenoxonium intermediate, a critical choice of solvent, and reagent addition order. The fluorinated dihydrobenzofuran product can be transformed into dihydrobenzofuran and benzofuran products decorated with a 2-trifluoromethyl group. The 3-trifluoromethylacyl substituted benzofurans rapidly form hydrates, which can be reduced to the corresponding alcohols.",

author = "Smith, {David T.} and Edon Vitaku and Njardarson, {Jon T.}",

note = "Funding Information: We would like to thank Dr. Andrei Astachkine and Pradipta Das from the University of Arizona for help with securing X-ray structures. Acknowledgment is made to the donors of the American Chemical Society Petroleum Research Fund for partial support of this research. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b01479",

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T1 - Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products

AU - Smith, David T.

AU - Vitaku, Edon

AU - Njardarson, Jon T.

N1 - Funding Information: We would like to thank Dr. Andrei Astachkine and Pradipta Das from the University of Arizona for help with securing X-ray structures. Acknowledgment is made to the donors of the American Chemical Society Petroleum Research Fund for partial support of this research. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/7/7

Y1 - 2017/7/7

N2 - A mild dearomatization enabled ortho-selective replacement of an aromatic C-H bond with a hexafluoroacetylacetone (hfacac) substituent has been developed. This reaction is dependent on a hypervalent iodine generated phenoxonium intermediate, a critical choice of solvent, and reagent addition order. The fluorinated dihydrobenzofuran product can be transformed into dihydrobenzofuran and benzofuran products decorated with a 2-trifluoromethyl group. The 3-trifluoromethylacyl substituted benzofurans rapidly form hydrates, which can be reduced to the corresponding alcohols.

AB - A mild dearomatization enabled ortho-selective replacement of an aromatic C-H bond with a hexafluoroacetylacetone (hfacac) substituent has been developed. This reaction is dependent on a hypervalent iodine generated phenoxonium intermediate, a critical choice of solvent, and reagent addition order. The fluorinated dihydrobenzofuran product can be transformed into dihydrobenzofuran and benzofuran products decorated with a 2-trifluoromethyl group. The 3-trifluoromethylacyl substituted benzofurans rapidly form hydrates, which can be reduced to the corresponding alcohols.

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Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products

Abstract

ASJC Scopus subject areas

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CCDC 1549516: Experimental Crystal Structure Determination

CCDC 1549515: Experimental Crystal Structure Determination

CCDC 1549517: Experimental Crystal Structure Determination

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Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1549516: Experimental Crystal Structure Determination

CCDC 1549515: Experimental Crystal Structure Determination

CCDC 1549517: Experimental Crystal Structure Determination

Cite this