Aminotrifluoromethylation of Olefins via Cyclic Amine Formation: Mechanistic Study and Application to Synthesis of Trifluoromethylated Pyrrolidines

Journal of the American Chemical Society

Volumn 137, Issue 14, 2015, Pages 4865-4873

  Kawamura, Shintaro ^a,b,c   Egami, Hiromichi ^a,c,d   Sodeoka, Mikiko ^a,b,c  

^a RIKEN   (Japan)

^b Elements Chemistry Laboratory   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^d UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHEMICAL REACTIONS; CHEMICAL SHIFT; COORDINATION REACTIONS; COPPER; CYCLIZATION; FLUORINE; IONIC LIQUIDS;

DYNAMIC EQUILIBRIA; EFFICIENT SYNTHESIS; HYPERVALENT IODINE; INTRAMOLECULAR CYCLIZATIONS; LEWIS ACID CATALYSTS; MECHANISTIC STUDIES; NMR CHEMICAL SHIFTS; PYRROLIDINE DERIVATIVES;

SYNTHESIS (CHEMICAL);

ALKENE; CUPROUS ION; PYRROLIDINE DERIVATIVE; AMINE; FLUOROCARBON; PYRROLIDINE;

AMINOTRIFLLUOROMETHYLATION; ARTICLE; CATALYST; ELECTROSPRAY MASS SPECTROMETRY; FLUORINE NUCLEAR MAGNETIC RESONANCE; NEGATIVE FEEDBACK; PROTEIN METHYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION TIME; SYNTHESIS; CATALYSIS; CHEMISTRY; CYCLIZATION; KINETICS; METHYLATION;

ALKENES; AMINES; CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLIZATION; FLUOROCARBONS; KINETICS; METHYLATION; PYRROLIDINES;

EID: 84927916096     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b02046     Document Type: Article

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146. For details of additive screening and optimization, see Supporting Information.
147. The stereochemical outcome may suggest the stepwise mechanism for the pyrrolidine formation.