Journal article
Arylthio-Metal Exchange of alpha-Arylthioalkanenitriles
Organic letters, v 16(1)
03 Jan 2014
PMID: 24328754
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
The addition of BuLi, Bu3MgLi, Et2ZnBuLi, or Me2CuLi to alpha-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high yield. The method addresses the challenge of improving the functional group tolerance and preventing polyalkylations.
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Details
- Title
- Arylthio-Metal Exchange of alpha-Arylthioalkanenitriles
- Creators
- Dinesh Nath - Duquesne UniversityMelanie C. Skilbeck - University of SheffieldIain Coldham - University of SheffieldFraser F. Fleming - Duquesne University
- Publication Details
- Organic letters, v 16(1)
- Publisher
- American Chemical Society; Washington, DC
- Number of pages
- 4
- Grant note
- IR/D; CHE 1111406; CHE-0963450 / National Science Foundation; National Science Foundation (NSF)
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000329472800017
- Scopus ID
- 2-s2.0-84891777017
- Other Identifier
- 991020898395504721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Organic