63697-19-8Relevant articles and documents
Direct Stereoselective β-Arylation of Enol Ethers by a Decarboxylative Heck-Type Reaction
Hachem, Mahmoud,Hoarau, Christophe,Schneider, Cédric
, (2020/04/15)
Despite remarkable advances to promote regio- and stereoselective decarboxylative arylation of inactivated olefins with benzoic acid derivatives, methodologies involving hetero-substituted alkenes are still lacking. Herein, PdII-catalyzed decarboxylative Heck coupling of α-alkoxyacrylates with (hetero)aryl carboxylic acids for the stereocontrolled production of (Z)-β-heteroarylated vinyl ethers is reported. This methodology offers a rational and step-economical route to the synthesis of attractive β-arylated α-alkoxy α,β-unsaturated carboxylates family which emerged as a relevant class of building blocks with different applications. Mechanistically, whereas electron rich benzoic acids undergo a PdII-catalyzed decarboxylation, electron-deficient substrates proceed through silver(I)-mediated decarboxylation, explaining thus the formation of stereoisomers (E) and (Z) of β-arylated vinyl ethers in presence of these latter.
Visible light driven hydro-/deuterodefunctionalization of anilines
Majek, Michal,Filace, Fabiana,Von Wangelin, Axel Jacobi
supporting information, p. 4518 - 4522 (2015/03/18)
The defunctionalization of anilines is an important strategy in aromatic-substitution chemistry. Herein, we report on visible light mediated hydro- and deuterodediazonations in solutions of DMF. The mild reaction conditions (DMF, RT, no additives) tolerate various functional groups and allow the site-specific introduction of D atoms to the arene. Mechanistic investigations indicate the participation of photoredox and radical chain pathways and competing abstraction of methyl and formyl hydrogen atoms from DMF.
Base-promoted protodeboronation of 2,6-disubstituted arylboronic acids
Lozada, Jerome,Liu, Zhibo,Perrin, David M.
supporting information, p. 5365 - 5368 (2014/06/23)
Facile based promoted deboronation of electron-deficient arylboronate esters was observed for arylboronates containing two ortho electron-withdrawing group (EWG) substituents. Among 30 representative boronates, only the diortho-substituted species underwe
