Rediscovering sulfinylamines as reagents for organic synthesis

Journal article

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-centered radicals, their use for the 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 highor low-valent sulfur, or even no sulfur at all.

Authors: Davies, T; Willis, M

• Publication status: Published
• Peer review status: Peer reviewed
• Publisher: Wiley
• Journal: Chemistry - A European Journal
• Volume: 27
• Issue: 35
• Pages: 8918-8927
• Publication date: 2021-06-01
• Acceptance date: 2021-02-22
• DOI: 10.1002/chem.202100321
• EISSN: 1521-3765
• ISSN: 0947-6539
• Language: English
• Keywords: FFR