Journal article
Sulfinylnitriles: Sulfinyl-Metal Exchange-Alkylation Strategies
Chemistry : a European journal, v 19(6), pp 2023-2029
04 Feb 2013
PMID: 23280544
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Adding organolithiums, Grignard reagents, or zincates to sulfinylnitriles triggers a facile sulfinylmetal exchange to afford N- or C-metalated nitriles. Sulfinylmagnesium exchangealkylations efficiently install quaternary and tertiary centers, even in the case of tertiary sulfinylnitriles that contain a highly acidic methine proton. -Sulfinylalkenenitriles afford moderately nucleophilic magnesiated nitriles, and the reactivity can be dramatically increased by conversion to the corresponding magnesiates. The sulfinyl-metal exchange is extremely fast, proceeds efficiently with quaternary, tertiary, and vinylic -sulfinylnitriles, and exhibits an exceptional functional group tolerance in nitrile alkylations.
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Details
- Title
- Sulfinylnitriles: Sulfinyl-Metal Exchange-Alkylation Strategies
- Creators
- Dinesh Nath - Duquesne UniversityFraser F. Fleming - Duquesne University
- Publication Details
- Chemistry : a European journal, v 19(6), pp 2023-2029
- Publisher
- Wiley
- Number of pages
- 7
- Grant note
- CHE 1111406; 0808996; 0421252 HRMS; 0614785 / National Science Foundation (USA); National Science Foundation (NSF)
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000314217100022
- Scopus ID
- 2-s2.0-84873294514
- Other Identifier
- 991020898392104721
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- Web of Science research areas
- Chemistry, Multidisciplinary