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Sulfone–Metal Exchange and Alkylation of Sulfonylnitriles
Journal article   Peer reviewed

Sulfone–Metal Exchange and Alkylation of Sulfonylnitriles

Xun Yang, Dinesh Nath, Michael R. Gau, Omar W. Steward and Fraser F. Fleming
Angewandte Chemie (International ed.), v 56(25), pp 7257-7260
12 Jun 2017
DOI: https://doi.org/10.1002/anie.201704028
PMID: 28464420
Featured in Collection :   UN Sustainable Development Goals @ Drexel

Abstract

alkylations lithiation nitriles sulfones synthetic methods
The first general sulfone–metal exchange is described. Treating substituted 2‐pyridylsulfonylacetonitriles with either BuLi or Bu3MgLi generates metalated nitriles that efficiently intercept a variety of electrophiles to afford quaternary nitriles. The 2‐pyridylsulfone is critical for the sulfone–metal exchange because chelation anchors the organometallic proximal to the electrophilic, tetrasubstituted sulfone to override complex‐induced deprotonation. Alkylating commercial 2‐pyridinesulfonylacetonitrile with mild bases, either K2CO3 or DBU, and subsequent sulfone–metal exchange and alkylation rapidly assembles quaternary nitriles by three alkylations, only one of which requires an organometallic reagent. Sulfones as latent organometallics: Sulfone–metal exchange of substituted 2‐pyridylsulfonylacetonitriles with either BuLi or Bu3MgLi generates metalated nitriles that alkylate a variety of electrophiles to efficiently install quaternary centers.

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8 citations in Web of Science
9 citations in Scopus

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Collaboration types
Domestic collaboration
Web of Science research areas
Chemistry, Multidisciplinary
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