Hypervalent Iodine(III) Reagents with Transferable Primary Amines: Structure and Reactivity on the Electrophilic α‑Amination of Stabilized Enolates

A new family of hypervalent iodine reagents containing transferable primary amine groups is described. Benziodoxolone-based reagents were synthesized on the gram-scale through operationally simple reactions in up to quantitative yields. These bench-stable solids were characterized by X-ray analysis...

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Bibliographic Details
Published in:Organic letters 2022-01, Vol.24 (2), p.776-781
Main Authors: Poeira, Diogo L, Negrão, Ana Cláudia R, Faustino, Hélio, Coelho, Jaime A. S, Gomes, Clara S. B, Gois, Pedro M. P, Marques, M. Manuel B
Format: Article
Language:English
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Summary:A new family of hypervalent iodine reagents containing transferable primary amine groups is described. Benziodoxolone-based reagents were synthesized on the gram-scale through operationally simple reactions in up to quantitative yields. These bench-stable solids were characterized by X-ray analysis and successfully employed in the α-amination of indanone-based β-ketoesters in up to 83% yield. Mechanistic studies indicate a substitution mechanism involving an electrophilic amine.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c04312