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Rediscovering Sulfinylamines as Reagents for Organic Synthesis
Author(s) -
Davies Thomas Q.,
Willis Michael C.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100321
Subject(s) - reactivity (psychology) , chemistry , organic synthesis , electrophile , sulfur , enantioselective synthesis , reagent , allylic rearrangement , organic chemistry , catalysis , combinatorial chemistry , radical , organic molecules , molecule , medicine , alternative medicine , pathology
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.