Direct access to N-unprotected tetrasubstituted propargylamines via direct catalytic alkynylation of N-unprotected trifluoromethyl ketimines

Direct catalytic alkynylation of N-unprotected trifluoromethyl ketimines is reported for the first time. A combination of catalytic amounts of diethylzinc and carboxylic acids promoted the reactions under proton-transfer conditions, allowing an unprecedented direct access to N-unprotected alpha-tetr...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 53; no. 47; pp. 6319 - 6322
Main Authors Morisaki, Kazuhiro, Morimoto, Hiroyuki, Ohshima, Takashi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Amines
Carboxylic acids
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Imines
Physical Sciences
Science & Technology
AMINATION
ASYMMETRIC ALKYNYLATION
HYDROGENATION
HIGHLY ENANTIOSELECTIVE CONSTRUCTION
ARYL HALIDES
ARYLATION
BOND FORMATION
ALDEHYDES
EFFICIENT
ALPHA-AMINOALLYLATION
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Summary:Direct catalytic alkynylation of N-unprotected trifluoromethyl ketimines is reported for the first time. A combination of catalytic amounts of diethylzinc and carboxylic acids promoted the reactions under proton-transfer conditions, allowing an unprecedented direct access to N-unprotected alpha-tetrasubstituted primary amines without additional deprotection steps.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc02194a