Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups

We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters,...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 24; pp. 9419 - 9424
Main Authors Govindan, Karthick, Chen, Nian-Qi, Chuang, Yu-Wei, Lin, Wei-Yu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.12.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PRIMARY AMINES
ACTIVATION
GENERATION
SULFUR
TRANSAMIDATION
MICHAEL ADDITION
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Summary:We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03541