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Rediscovering sulfinylamines as reagents for organic synthesis - Deleted

DOI: 10.1002/chem.202100321 DOI Help

Authors: Thomas Q. Davies (University of Oxford Bodleian Library) , Michael C. Willis (University of Oxford)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Chemistry – A European Journal

State: Published (Approved)
Published: April 2021

Abstract: Sulfinylamines (R‐N=S=O), monoaza analogues of sulfur dioxide, have been known for well over a century, and their reactivity as sulfur electrophiles and in Diels‐Alder reactions is well‐established. However, they have only rarely been used in organic synthesis in recent decades despite the increasing prominence of compounds containing N=S=O functionality, such as sulfoximines and sulfonimidamides. This Minireview aims to bring wider visibility to the unique chemistry enabled by this class of compounds. We focus on advances from the last 10 years, including the first examples of their use in the one‐pot syntheses of sulfoximines and sulfonimidamides. Also covered are the reactions of sulfinylamines with carbon‐centred radicals, their use for formation of heterocycles through cycloadditions, and catalytic enantioselective allylic oxidation of alkenes via a hetero‐ene reaction. These examples highlight the different reactivity modes of sulfinylamines and their underappreciated potential for forming molecules which contain high‐ or low‐valent sulfur, or even no sulfur at all.

Journal Keywords: organosulfur; sulfinylamine; sulfoximines; sulfonimidamide; cycloaddition

Subject Areas: Chemistry


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Organic Chemistry Chemistry

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