A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides | Zendy

Mingyan Ding | Zendy; ZeXin Zhang | Zendy; Thomas Q. Davies | Zendy; Michael C. Willis | Zendy

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A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides

Author(s) -

Mingyan Ding,

ZeXin Zhang,

Thomas Q. Davies,

Michael C. Willis

Publication year - 2022

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.2c00347

Subject(s) - hypervalent molecule , reagent , chemistry , primary (astronomy) , silylation , alkyl , aryl , combinatorial chemistry , amine gas treating , modular design , organic chemistry , catalysis , computer science , physics , astronomy , operating system

A new N -silyl sulfinylamine reagent allows the rapid preparation of a broad range of (hetero)aryl, alkenyl, and alkyl primary sulfinamides, using Grignard, organolithium, or organozinc reagents to introduce the carbon fragment. Treatment of these primary sulfinamides with an amine in the presence of a hypervalent iodine reagent leads directly to NH-sulfonimidamides. This two-step sequence is straightforward to perform and provides a modular approach to sulfonimidamides, allowing ready variation of both reaction components, including primary and secondary amines.

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