In Situ Generation of N-Triflylimino-λ3-iodanes: Application to Imidation of Phosphines and Catalytic α-Amidation of 1,3-Dicarbonyl Compounds

Shun Sunagawa; Fumiya Morisaki; Takafumi Baba; Akira Tsubouchi; Akira Yoshimura; Kazunori Miyamoto; Masanobu Uchiyama; Akio Saito

doi:10.1021/acs.orglett.2c02264

In Situ Generation of N-Triflylimino-λ³-iodanes: Application to Imidation of Phosphines and Catalytic α-Amidation of 1,3-Dicarbonyl Compounds

Org Lett. 2022 Jul 22;24(28):5230-5234. doi: 10.1021/acs.orglett.2c02264. Epub 2022 Jul 13.

Authors

Shun Sunagawa¹, Fumiya Morisaki¹, Takafumi Baba¹, Akira Tsubouchi¹, Akira Yoshimura², Kazunori Miyamoto³, Masanobu Uchiyama^{3

4}, Akio Saito¹

Affiliations

¹ Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan.
² Faculty of Pharmaceutical Sciences, Aomori University, 2-3-1 Kobata, Aomori 030-0943, Japan.
³ Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
⁴ Research Initiative for Supra-Materials (RISM), Shinshu University, Ueda 386-8567, Japan.

PMID: 35822905
DOI: 10.1021/acs.orglett.2c02264

Abstract

We describe the imidation of phosphines and α-amidation of 1,3-dicarbonyl compounds using N-triflylimino-λ³-iodane, which is generated in situ from iodosylarene and triflylamide without any other additives. Furthermore, the imino-λ³-iodane catalytically generated from an iodoarene precatalyst with oxone and triflylamide promotes α-amidation of 1,3-dicarbonyl compounds, representing the first method catalyzed by imino-λ³-iodane.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis*
Phosphines

Substances

Phosphines
phosphine