14618-12-3Relevant articles and documents
General access to C-centered radicals: Combining a bioinspired photocatalyst with boronic acids in aqueous media
Bloom, Steven,Chilamari, Maheshwerreddy,Immel, Jacob R.
, p. 12727 - 12737 (2020/11/18)
Carbon-centered radicals are indispensable building blocks for modern synthetic chemistry. In recent years, visible light photoredox catalysis has become a promising avenue to access C-centered radicals from a broad array of latent functional groups, including boronic acids. Herein, we present an aqueous protocol wherein water features a starring role to help transform aliphatic, aromatic, and heteroaromatic boronic acids to C-centered radicals with a bioinspired flavin photocatalyst. These radicals are used to deliver a diverse pool of alkylated products, including three pharmaceutically relevant compounds, via open-shell conjugate addition to disparate Michael acceptors. The mechanism of the reaction is investigated by computational studies, deuterium labeling, radical-trapping experiments, and spectroscopic analysis.
Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate
Coutant, Eloi P.,Hervin, Vincent,Gagnot, Glwadys,Ford, Candice,Baatallah, Racha,Janin, Yves L.
supporting information, p. 2853 - 2860 (2018/11/26)
We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates - using Suzuki-Miyaura coupling or cycloadditions - before undertaking the oximation step - provided accesses to further α-amino esters. Moreover, other pathways to α-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl β-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.
Fe(HSO4)3 : An efficient, heterogeneous and reusable catalyst for C-alkylation of β-dicarbonyl compounds
Khafajeh, Samaneh,Akhlaghinia, Batool,Rezazadeh, Soodabeh,Eshghi, Hossein
, p. 1903 - 1912 (2015/02/05)
Fe(HSO4)3(FHS) was used as an efficient catalyst for the heterogeneous addition of a series of benzylic and allylic alcohols to various β-dicarbonyl compounds, which afforded moderate to excellent yields of C-alkylated products in 1,2-dichloroethane. In comparison with the previous methods, the present research surprisingly exhibited higher reaction yields without formation of any by-products which could be formed by self-condensation of alcohols. Moreover, the catalyst can be readily recovered and reused up to five times with almost maintained reactivity and yields.