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.
Photochemical Organocatalytic Borylation of Alkyl Chlorides, Bromides, and Sulfonates / Mazzarella D.; Magagnano G.; Schweitzer-Chaput B.; Melchiorre P.. - In: ACS CATALYSIS. - ISSN 2155-5435. - STAMPA. - 9:7(2019), pp. 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.