Azasulfur(<scp>iv</scp>) derivatives of sulfite and sulfinate esters by formal S–S bond insertion of dichloramines

Wu, Peng; Demaerel, Joachim; Statham, Benjamin J.; Bolm, Carsten

doi:10.1039/d4sc00500g

Chem. Sci.

2024

DOI: 10.1039/d4sc00500g

|View full text |Cite

Azasulfur(iv) derivatives of sulfite and sulfinate esters by formal S–S bond insertion of dichloramines

Peng Wu,

Joachim Demaerel,

Benjamin J. Statham

et al.

Abstract: Azasulfur(VI) compounds such as sulfoximines and sulfonimidamides are attractive due to the unique properties of the S=N bond. While the synthesis for these carbon-attached sulfonimidoyl derivatives is well-established, the situation...

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

References 66 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

2‐Methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl Fluoride: A Bench‐Stable Alternative to SOF₄ as Precursor to N,O‐Substituted S(VI) Compounds

Lional,

Miloserdov,

Zuilhof

2024

Angewandte Chemie

View full text Add to dashboard Cite

S(VI) compounds with multiple N or O substituents are often difficult to make and several crucial routes, such as multimodal SuFEx (Sulfur (VI) Fluoride Exchange) chemistry, rely on the highly useful but hazardous SOF4 gas. Safety issues and inaccessibility of SOF4 strongly hamper the developments of these organic compounds. Here we describe the synthesis and applications of 2‐methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl fluoride (ImSF), a novel bench‐stable analogue of SOF4. ImSF is synthesized on a gram scale via a double fluorination of t‐OctNSO. We show ImSF can undergo substitution reactions with phenols and amines, which lead to sulfurimidates and sulfuramidimidates, respectively, the intrinsically chiral analogous of medicinally relevant sulfates and sulfamates in which an S=O moiety is replaced by S=NR unit. Finally we demonstrate that such substitutions can occur enantiospecifically, providing the first entry to chiral sulfurimidates and sulfuramidimidates.

show abstract

2‐Methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl Fluoride: A Bench‐Stable Alternative to SOF₄ as Precursor to N,O‐Substituted S(VI) Compounds

Lional,

Miloserdov,

Zuilhof

2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

2‐Methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl Fluoride: A Bench‐Stable Alternative to SOF₄ as Precursor to N,O‐Substituted S(VI) Compounds

Lional,

Miloserdov,

Zuilhof

2024

Angew Chem Int Ed

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Azasulfur(iv) derivatives of sulfite and sulfinate esters by formal S–S bond insertion of dichloramines

Abstract: Azasulfur(VI) compounds such as sulfoximines and sulfonimidamides are attractive due to the unique properties of the S=N bond. While the synthesis for these carbon-attached sulfonimidoyl derivatives is well-established, the situation...

Cited by 2 publications

References 66 publications

2‐Methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl Fluoride: A Bench‐Stable Alternative to SOF₄ as Precursor to N,O‐Substituted S(VI) Compounds

2‐Methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl Fluoride: A Bench‐Stable Alternative to SOF₄ as Precursor to N,O‐Substituted S(VI) Compounds

2‐Methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl Fluoride: A Bench‐Stable Alternative to SOF₄ as Precursor to N,O‐Substituted S(VI) Compounds

Contact Info

Product

Resources

About

Azasulfur(iv) derivatives of sulfite and sulfinate esters by formal S–S bond insertion of dichloramines

Abstract: Azasulfur(VI) compounds such as sulfoximines and sulfonimidamides are attractive due to the unique properties of the S=N bond. While the synthesis for these carbon-attached sulfonimidoyl derivatives is well-established, the situation...

Cited by 2 publications

References 66 publications

2‐Methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl Fluoride: A Bench‐Stable Alternative to SOF4 as Precursor to N,O‐Substituted S(VI) Compounds

2‐Methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl Fluoride: A Bench‐Stable Alternative to SOF4 as Precursor to N,O‐Substituted S(VI) Compounds

2‐Methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl Fluoride: A Bench‐Stable Alternative to SOF4 as Precursor to N,O‐Substituted S(VI) Compounds

Contact Info

Product

Resources

About

2‐Methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl Fluoride: A Bench‐Stable Alternative to SOF₄ as Precursor to N,O‐Substituted S(VI) Compounds

2‐Methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl Fluoride: A Bench‐Stable Alternative to SOF₄ as Precursor to N,O‐Substituted S(VI) Compounds

2‐Methylimidazole‐1‐(N‐tert‐octyl)sulfonimidoyl Fluoride: A Bench‐Stable Alternative to SOF₄ as Precursor to N,O‐Substituted S(VI) Compounds