A method for the Ni-catalyzed arylboration of unactivated monosubstituted, 1,1-disubstituted and trisubstituted alkenes is disclosed. The reaction is notable in that it converts highly substituted alkenes, arylbromides and diboron reagents to products that contain a quaternary carbon and a synthetically versatile carbon-boron bond with control of stereoselectivity and regioselectivity. In addition, the method is demonstrated to be useful for the synthesis of saturated nitrogen heterocycles, which are important motifs in pharmaceutical compounds. Finally, due to the unusual reactivity demonstrated, the mechanistic details of the reaction were studied with both computational and experimental techniques.
A method
for amide-directed Ni-catalyzed diastereoselective arylboration
of cyclopentenes is disclosed. The reaction allows for the synthesis
of sterically congested cyclopentane scaffolds that contain an easily
derivatized boronic ester and amide functional handles. The nature
of the amide directing group and its influence on the reaction outcome
are investigated and ultimately reflect a predictably selective reaction
based on the solvent and base counterion.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.