Synthesis of β‑Aminoenones via Cross-Coupling of In-Situ-Generated Isocyanides with 1,3-Dicarbonyl Compounds

An efficient and practical strategy for the synthesis of β-aminoenones from a three-component reaction was developed. Ethyl bromodifluoroacetate serves as a C1 source in this strategy, forming isocyanides in situ with primary amines. This reaction represents the first example of utilization of readi...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2018-08, Vol.20 (16), p.4777-4781
Main Authors: Ma, Xingxing, Zhou, Yao, Song, Qiuling
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An efficient and practical strategy for the synthesis of β-aminoenones from a three-component reaction was developed. Ethyl bromodifluoroacetate serves as a C1 source in this strategy, forming isocyanides in situ with primary amines. This reaction represents the first example of utilization of readily available starting materials to generate isocyanides in situ and sequentially fully converted to β-aminoenones, avoiding the generation of byproduct imines and overinsertion products. The mechanism study suggested that this method involves activation of two C­(sp3)–F bonds and the formation of isocyanides, which might nourish both isocyanide chemistry and fluorine chemistry.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01888