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Direct reductive coupling of secondary amides: chemoselective formation of vicinal diamines and vicinal amino alcohols
- Source :
- Chemical Communications. 51:1096-1099
- Publication Year :
- 2015
- Publisher :
- Royal Society of Chemistry (RSC), 2015.
-
Abstract
- We report the first one-pot reductive homocoupling reaction of secondary amides and cross-coupling reaction of secondary amides with ketones to give secondary vicinal diamines and amino alcohols. This method relies on the direct generation of α-amino carbon radicals from secondary amides by activation with trifluoromethanesulfonic anhydride, partial reduction with triethylsilane and samarium diiodide-mediated single-electron transfer. The reactions were run under mild conditions and tolerated several functional groups.
- Subjects :
- Molecular Structure
Chemistry
Trifluoromethanesulfonic anhydride
Radical
Metals and Alloys
chemistry.chemical_element
General Chemistry
Diamines
Amides
Amino Alcohols
Medicinal chemistry
Catalysis
Surfaces, Coatings and Films
Electronic, Optical and Magnetic Materials
Samarium
chemistry.chemical_compound
Materials Chemistry
Ceramics and Composites
Organic chemistry
Triethylsilane
Oxidation-Reduction
Vicinal
Subjects
Details
- ISSN :
- 1364548X and 13597345
- Volume :
- 51
- Database :
- OpenAIRE
- Journal :
- Chemical Communications
- Accession number :
- edsair.doi.dedup.....69e8d8784a2d4ba273ebae0520739d30