ArticleEuropean journal of organic chemistry2015
Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs.
Article in European journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Harnessing the Reactivity of Sulfinate Salts With Cystine: An Umpolung Approach to Residue-Specific Peptide Modification.Angewandte Chemie (International ed. in English) · 2026Article
- Palladium-Catalyzed Sulfinylation of Aryl- and Alkenylborons with Sulfinate Esters.Organic letters · 2021Article
- Synthesis of NACS omega · 2021Article
- Sulfenylation of Arenes with Ethyl Arylsulfinates in Water.ACS omega · 2020Article
- KACS omega · 2020Article
- Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis.Molecules (Basel, Switzerland) · 2020Review
- Synthesis of Imidazole-Based Medicinal Molecules Utilizing the van Leusen Imidazole Synthesis.Pharmaceuticals (Basel, Switzerland) · 2020Review
- Tough and Functional Cross-linked Bioplastics from Sheep Wool Keratin.Scientific reports · 2019Article
- Asmic: An Exceptional Building Block for Isocyanide Alkylations.Organic letters · 2018Article
- An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks.RSC advances · 2018Article
- Alkenyl Isocyanide Conjugate Additions: A Rapid Route to γ-Carbolines.Angewandte Chemie (International ed. in English) · 2017Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Alkyl sulfinates function as formal nucleophiles in Mannich-type reactions to give sulfonyl formamides, which are readily dehydrated to the corresponding sulfonylmethyl isonitriles. The efficient, two-step synthesis provides a general route to sulfonylmethyl isonitriles from readily available methyl sulfinates or thiols. Mechanistic analysis reveals that the unusual nucleophlicity of the alkyl sulfinates arises from the in situ release of sulfinic acids.
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Registered trials
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