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

Diogo L. Poeira, Ana Cláudia Ribeiro Negrão, Hélio Faustino, Jaime A. S. Coelho, Clara S. B. Gomes, Pedro M. P. Gois, M. Manuel B. Marques

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)776-781
Number of pages6
JournalOrganic Letters
Volume24
Issue number2
DOIs
Publication statusPublished - 21 Jan 2022

Fingerprint

Dive into the research topics of 'Hypervalent Iodine(III) Reagents with Transferable Primary Amines: Structure and Reactivity on the Electrophilic α-Amination of Stabilized Enolates'. Together they form a unique fingerprint.

Cite this