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Green and rapid acid-catalyzed ynamide skeletal rearrangement and stereospecific functionalization with anisole derivatives.
- Source :
- Green Chemistry; 10/21/2023, Vol. 25 Issue 20, p8124-8133, 10p
- Publication Year :
- 2023
-
Abstract
- Environmentally friendly acid-catalyzed ynamide N–C<subscript>sp</subscript> bond cleavage, skeletal rearrangement and chemo-, regio- and stereospecific functionalization with nucleophiles are of great interest in synthetic chemistry. However, such transformations present remarkable regio- and stereospecific challenges due to the biased carbon–carbon (α and β) triple bonds in ynamides. Herein, we developed a greener and faster acid-catalyzed ynamide N–C<subscript>sp</subscript> bond fission, skeletal rearrangement and stereospecific functionalization with nucleophilic anisole derivatives to produce thermodynamically unstable challenging cis-alkene tethered indole scaffolds in a very short reaction time (5–10 min). The key features of this transformation are its transition-metal-free nature, broad scope, ease of handling, simple setup, mild reaction conditions, atom/step/time economy, and the gram-scale experiment. Most importantly, <superscript>13</superscript>C-isotope labeling experiments in mechanistic studies confirmed the alkyne-carbon position in the rearrangement process. The green chemistry metrics evaluation and EcoScale score (75 on a scale of 0–100) indicate that our transformation is safer, environmentally friendly, and economically feasible. [ABSTRACT FROM AUTHOR]
- Subjects :
- ANISOLE
SCISSION (Chemistry)
YNAMIDES
NUCLEOPHILES
INDOLE
REARRANGEMENTS (Chemistry)
Subjects
Details
- Language :
- English
- ISSN :
- 14639262
- Volume :
- 25
- Issue :
- 20
- Database :
- Complementary Index
- Journal :
- Green Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 172981198
- Full Text :
- https://doi.org/10.1039/d3gc02460a