5359-46-6Relevant academic research and scientific papers
Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation
da Silva, Amanda F.,Afonso, Marco A. S.,Cormanich, Rodrigo A.,Jurberg, Igor D.
, p. 5648 - 5653 (2020/04/22)
A visible-light-promoted photochemical protocol is reported for the coupling of aryldiazoacetates with boronic acids. This photochemical reaction shows great enhancement compared to the same protocol performed in the absence of light. Except for a few cases, the room temperature coupling in the dark (thermal process) generally does not work. When it does, it is likely to also involve free carbenes as key intermediates. Alternatively, photochemical reactions show a broad scope, can be performed under air and tolerate a wide variety of functional groups. Reaction-evolution monitoring, DFT calculations and control experiments have been used to evaluate the main aspects of this intricate mechanistic scenario. Biologically active molecules Adiphenine, Benactyzine and Aprophen have been prepared as examples of synthetic applications.
RhI-Catalyzed Stille-Type Coupling of Diazoesters with Aryl Trimethylstannanes
Liu, Zhen,Xia, Ying,Feng, Sheng,Wang, Shuai,Qiu, Di,Zhang, Yan,Wang, Jianbo
, p. 1379 - 1384 (2015/09/15)
A RhI-catalyzed cross-coupling of diazoester with arylstannane was developed. This reaction represents the first Stille-type coupling that uses a diazo compound as the coupling partner. The reaction is operationally simple and can be carried out under mild conditions, thus providing an alternative approach for the synthesis of α-aryl esters. RhI-carbene migratory insertion process is suggested to be involved as the key step in this Stille-type coupling.
Rhodium-catalyzed cross-coupling reaction of arylboronates and diazoesters and tandem alkylation reaction for the synthesis of quaternary r,r-heterodiaryl carboxylic esters
Tsoi, Yuk-Tai,Zhou, Zhongyuan,Yu, Wing-Yiu
supporting information; experimental part, p. 5370 - 5373 (2011/12/03)
A rhodium-catalyzed one-pot three-component coupling reaction was developed for the synthesis of quaternary α,α-heterodiaryl carboxylic esters. This reaction involves cross-coupling of the arylrhodium(I) complexes with R-aryldiazoacetates to form oxa-π-al
