126002-57-1Relevant articles and documents
1-Ethylpiperidinium Hypophosphite: A Practical Mediator for Radical Carbon-Carbon Bond Formation
Jang, Doo Ok,Cho, Dae Hyan,Chung, Chan-Moon
, p. 1923 - 1924 (2001)
1-Ethylpiperidinium hypophosphite could be used efficiently as radical chain carrier in the intermolecular carbon-carbon bond formation without using excess of alkenes under mild reaction conditions.
Decarboxylative Giese-Type Reaction of Carboxylic Acids Promoted by Visible Light: A Sustainable and Photoredox-Neutral Protocol
Ramirez, Nieves P.,Gonzalez-Gomez, Jose C.
, p. 2154 - 2163 (2017)
We describe herein a transition-metal-free method for the decarboxylative generation of radicals from carboxylic acids and their 1,4-addition to Michael acceptors. The Fukuzumi catalyst (9-mesitylene-10-methylacridinium perchlorate, [Acr-Mes]ClO4) enabled this transformation under visible-light irradiation at room temperature with CO2 as the only byproduct. The scope and limitations of this protocol were examined by using a range of Michael acceptors (15 examples) and carboxylic acids (18 examples). The use of 3-hydroxypivalic acid in this protocol allowed the straightforward formation of a diastereomerically pure δ-lactone. Moreover, when a homoallylic acid was used, a radical cascade reaction took place with the formation of three C–C bonds.
Catalyst-Controlled C-H Functionalization of Adamantanes Using Selective H-Atom Transfer
Yang, Hai-Bin,Feceu, Abigail,Martin, David B. C.
, p. 5708 - 5715 (2019)
A method for the direct functionalization of diamondoids has been developed using photoredox and H atom transfer catalysis. This C-H alkylation reaction has excellent chemoselectivity for the strong 3° C-H bonds of adamantanes in polyfunctional molecules.
Catalyst-Free Decarboxylation of Carboxylic Acids and Deoxygenation of Alcohols by Electro-Induced Radical Formation
Chen, Xiaoping,Luo, Xiaosheng,Peng, Xiao,Guo, Jiaojiao,Zai, Jiantao,Wang, Ping
supporting information, p. 3226 - 3230 (2020/02/27)
Electro-induced reduction of redox active esters and N-phthalimidoyl oxalates derived from naturally abundant carboxylic acids and alcohols provides a sustainable and inexpensive approach to radical formation via undivided electrochemical cells. The resulting radicals are trapped by an electron-poor olefin or hydrogen atom source to furnish the Giese reaction or reductive decarboxylation products, respectively. A broad range of carboxylic acid (1°, 2°, and 3°) and alcohol (2° and 3°) derivatives are applicable in this catalyst-free reaction, which tolerated a diverse range of functional groups. This method features simple operation, is a sustainable platform, and has broad application.