Azidodifluoromethanide (N3CF2-): In Situ Generation and Nucleophilic Addition to Aldehydes

Colby Barrett; Anushan Alagaratnam; Alexander Knieb; Christopher J. Koch; G. K.Surya Prakash

doi:10.1021/acs.orglett.4c02144

Azidodifluoromethanide (N₃CF₂^-): In Situ Generation and Nucleophilic Addition to Aldehydes

Colby Barrett
, Anushan Alagaratnam
, Alexander Knieb
, Christopher J. Koch
, G. K.Surya Prakash

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

4 Scopus citations

Abstract

A facile one-pot approach for the azidodifluoromethylation of aldehydes via in situ-generated azidodifluoromethenide (N₃CF₂^-) utilizing commercially available TMSCF₂Br and NaN₃ is disclosed. The formed O-silyl ether products are obtained in yields of up to 91% in short reaction times at ambient temperature. Examples of both inter- and intramolecular [3 + 2] azide-alkyne cycloaddition reactions of the installed azidodifluoromethyl handles are also presented, demonstrating the prospective synthetic and biochemical functionality and utility.

Original language	English (US)
Pages (from-to)	6385-6389
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	30
DOIs	https://doi.org/10.1021/acs.orglett.4c02144
State	Published - Aug 2 2024
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.4c02144

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title = "Azidodifluoromethanide (N3CF2-): In Situ Generation and Nucleophilic Addition to Aldehydes",

abstract = "A facile one-pot approach for the azidodifluoromethylation of aldehydes via in situ-generated azidodifluoromethenide (N3CF2-) utilizing commercially available TMSCF2Br and NaN3 is disclosed. The formed O-silyl ether products are obtained in yields of up to 91\% in short reaction times at ambient temperature. Examples of both inter- and intramolecular [3 + 2] azide-alkyne cycloaddition reactions of the installed azidodifluoromethyl handles are also presented, demonstrating the prospective synthetic and biochemical functionality and utility.",

author = "Colby Barrett and Anushan Alagaratnam and Alexander Knieb and Koch, \{Christopher J.\} and Prakash, \{G. K.Surya\}",

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doi = "10.1021/acs.orglett.4c02144",

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T1 - Azidodifluoromethanide (N3CF2-)

T2 - In Situ Generation and Nucleophilic Addition to Aldehydes

AU - Barrett, Colby

AU - Alagaratnam, Anushan

AU - Knieb, Alexander

AU - Koch, Christopher J.

AU - Prakash, G. K.Surya

PY - 2024/8/2

Y1 - 2024/8/2

N2 - A facile one-pot approach for the azidodifluoromethylation of aldehydes via in situ-generated azidodifluoromethenide (N3CF2-) utilizing commercially available TMSCF2Br and NaN3 is disclosed. The formed O-silyl ether products are obtained in yields of up to 91% in short reaction times at ambient temperature. Examples of both inter- and intramolecular [3 + 2] azide-alkyne cycloaddition reactions of the installed azidodifluoromethyl handles are also presented, demonstrating the prospective synthetic and biochemical functionality and utility.

AB - A facile one-pot approach for the azidodifluoromethylation of aldehydes via in situ-generated azidodifluoromethenide (N3CF2-) utilizing commercially available TMSCF2Br and NaN3 is disclosed. The formed O-silyl ether products are obtained in yields of up to 91% in short reaction times at ambient temperature. Examples of both inter- and intramolecular [3 + 2] azide-alkyne cycloaddition reactions of the installed azidodifluoromethyl handles are also presented, demonstrating the prospective synthetic and biochemical functionality and utility.

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UR - https://www.scopus.com/pages/publications/85199106772#tab=citedBy

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AN - SCOPUS:85199106772

SN - 1523-7060

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SP - 6385

EP - 6389

JO - Organic Letters

JF - Organic Letters

IS - 30

ER -

Azidodifluoromethanide (N₃CF₂^-): In Situ Generation and Nucleophilic Addition to Aldehydes

Abstract

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