1312712-22-3Relevant articles and documents
Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters
Wang, Bingbing,Peng, Pan,Ma, Wan,Liu, Zhao,Huang, Cheng,Cao, Yangmin,Hu, Ping,Qi, Xiaotian,Lu, Qingquan
supporting information, p. 12985 - 12991 (2021/09/03)
Herein, a fast, scalable, and transition-metal-free borylation of alkyl halides (X = I, Br, Cl) enabled by electroreduction is reported. This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current. More than 70 examples, including the late-stage borylation of natural products and drug derivatives, are furnished at room temperature, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies disclosed that B2cat2 serves as both a reagent and a cathodic mediator, enabling electroreduction of difficult-to-reduce alkyl bromides or chlorides at a low potential.
Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor–Acceptor Complex
Sandfort, Frederik,Strieth-Kalthoff, Felix,Klauck, Felix J. R.,James, Michael J.,Glorius, Frank
supporting information, p. 17210 - 17214 (2018/11/10)
A deaminative strategy for the borylation of aliphatic primary amines is described. Alkyl radicals derived from the single-electron reduction of redox-active pyridinium salts, which can be isolated or generated in situ, were borylated in a visible light-mediated reaction with bis(catecholato)diboron. No catalyst or further additives were required. The key electron donor–acceptor complex was characterized in detail by both experimental and computational investigations. The synthetic potential of this mild protocol was demonstrated through the late-stage functionalization of natural products and drug molecules.
