Applications of 2‑Chloro-3,3,3-trifluoroprop-1-ene (HCFO-1233xf): A Rapid Entry to Various β‑Substituted-trifluoromethyl-ethenes

An efficient base-promoted reaction of O-, N-, and S-nucleophiles with 2-chloro-3,3,3-trifluoprop-1-ene (HCFO-1233xf) is described providing access to various β-substituted-trifluoromethyl-ethenes under mild reaction conditions. Mechanistic investigations shed some light on the regio-, chemo-, and s...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 22; no. 9; pp. 3479 - 3484
Main Authors Meyer, Daniel, El Qacemi, Myriem
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.05.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PHARMACEUTICALS
STEREOCHEMISTRY
REACTIVITY
FLUORINE
ALPHA
GENERATION
CF3 GROUP
ADDITIONS
NUCLEOPHILIC VINYLIC SUBSTITUTION
DERIVATIVES
Online AccessGet full text

Cover

More Information
Summary:An efficient base-promoted reaction of O-, N-, and S-nucleophiles with 2-chloro-3,3,3-trifluoprop-1-ene (HCFO-1233xf) is described providing access to various β-substituted-trifluoromethyl-ethenes under mild reaction conditions. Mechanistic investigations shed some light on the regio-, chemo-, and stereoselectivities observed. The olefins prepared represent attractive intermediates in chemical discovery: some applications include their conversion to pyrrolidines via a [3 + 2] dipolar cycloaddition reaction. These weakly basic amines represent novel synthons that could be readily elaborated through a range of reactions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00931