Expedient copper-catalyzed borylation reactions using amino acids as ligands

Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse

“…It was observed that by altering the catalytic system for this reaction, the selectivity of the reaction could be changed from borylative cyclization previously observed (section ) to boryl substitution . Deng et al also showed that amino acids could be used as ligands in the copper-catalyzed borylation of primary and secondary alkyl bromides . Copper nanoparticles have also been shown to catalyze the borylation of primary and secondary alkyl halides with B 2 pin 2 by both the Chung and the Xu groups.…”

“…752 Deng et al also showed that amino acids could be used as ligands in the copper-catalyzed borylation of primary and secondary alkyl bromides. 753 Copper nanoparticles have also been shown to catalyze the borylation of primary and secondary alkyl halides with B 2 pin 2 by both the Chung 754 and the Xu 755 groups.…”

Acridine-based copper(i) PNP pincer complexes: catalysts for alkyne hydroboration and borylation of aryl halides

“…A number of methods have been established for the synthesis of arylboronates from aryl halides employing catalytic copper/NHC, 9 copper/phosphine, 10 and other copper-based systems. 11 In addition, various copper-catalysed reactions converting alkyl halides to alkylboronates have been reported. 12 Many of these copper catalysts feature monodentate supporting ligands, and we proposed that developing new classes of copper catalysts bearing bulky, tridentate PNP ligands might furnish catalyst systems that might be more stable at elevated temperatures.…”

Saturated Boronic Acids, Boronates, and Trifluoroborates: An Update on Their Synthetic and Medicinal Chemistry

“…Thus, copper nanoparticles appeared to be catalytically active in the alkyl bromide borylation under phosphine-free conditions (Table 6, entry 5). [174] The ligand-assisted Cu-catalyzed borylations were based on the CuCl/Br/IÀ PPh 3 (entries 1-3 and 6), [169,170,175] Cu(OTf) 2 -dimethylglycine (entry 7), [176] CuCl 2 -1,3-dimesitylimidazol-2-ylidene (IMes; entry 8), [177] or SIMesCuCl [178] (entry 9) as the precatalysts. B 2 Pin 2 , B 2 Neop 2 and PinB-BDan (Dan: 1,8-diaminonaphtalene) were used as the boronation reagents; also, one-pot synthesis of cyclic secondary trifluoroborates was described by Molander and co-workers employing the use of polymer-supported PPh 3 (entry 4).…”