Reported herein is a photochemical strategy for the borylation of alkyl halides using bis(catecholato)diboron as the boron source. This method exploits the ability of a nucleophilic dithiocarbonyl anion organocatalyst to generate radicals via an SN2-based photochemical catalytic mechanism, which is not reliant on the redox properties of the substrates. Therefore, it grants access to alkyl boronic esters from readily available but difficult-to-reduce electrophiles, including benzylic and allylic chlorides, bromides, and mesylates, which were inert to or unsuitable for previously reported metal-free borylation protocols.
Mazzarella D., Magagnano G., Schweitzer-Chaput B., Melchiorre P. (2019). Photochemical Organocatalytic Borylation of Alkyl Chlorides, Bromides, and Sulfonates. ACS CATALYSIS, 9(7), 5876-5880 [10.1021/acscatal.9b01482].
Photochemical Organocatalytic Borylation of Alkyl Chlorides, Bromides, and Sulfonates
Magagnano G.;Melchiorre P.
Ultimo
Supervision
2019
Abstract
Reported herein is a photochemical strategy for the borylation of alkyl halides using bis(catecholato)diboron as the boron source. This method exploits the ability of a nucleophilic dithiocarbonyl anion organocatalyst to generate radicals via an SN2-based photochemical catalytic mechanism, which is not reliant on the redox properties of the substrates. Therefore, it grants access to alkyl boronic esters from readily available but difficult-to-reduce electrophiles, including benzylic and allylic chlorides, bromides, and mesylates, which were inert to or unsuitable for previously reported metal-free borylation protocols.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
