1360914-08-4Relevant articles and documents
Borylation of primary and secondary alkyl bromides catalyzed by Cu2O nanoparticles
Zhou, Xin-Feng,Wu, Ya-Dong,Dai, Jian-Jun,Li, Yong-Jia,Huang, Yu,Xu, Hua-Jian
, p. 46672 - 46676 (2015)
A Cu2O nanoparticle catalyzed borylation of activated and unactivated alkyl bromides is developed, using bis(pinacolato)diboron as a boron source. To the best of our knowledge this is the first report of a heterogeneous Cu2O nanocata
Electrochemically promoted decarboxylative borylation of alkyl N-hydroxyphthalimide esters
Dai, Jian-Jun,Teng, Xin-Xin,Fang, Wen,Xu, Jun,Xu, Hua-Jian
, p. 1555 - 1558 (2021/10/01)
An electrochemically promoted decarboxylative borylation reaction is reported. The reaction proceeds under mild conditions in an undivided cell without use of transition metal- or photo-catalysts. The key feature of the reaction is the compatibility of di
Evaluation of the role of graphene-based Cu(i) catalysts in borylation reactions
Cid, M. B.,Díaz, Cristina,Franco, Mario,Lamsabhi, Al Mokhtar,Sainz, Raquel,Tortosa, Mariola
, p. 3501 - 3513 (2021/06/06)
Carbon-supported catalysts have been considered as macromolecular ligands which modulate the activity of the metallic catalytic center. Understanding the properties and the factors that control the interactions between the metal and support allows a fine tuning of the catalyzed processes. Although huge effort has been devoted to comprehending binding energies and charge transfer for single atom noble metals, the interaction of graphenic surfaces with cheap and versatile Cu(i) salts has been scarcely studied. A methodical experimental and theoretical analysis of different carbon-based Cu(i) materials in the context of the development of an efficient, general, scalable, and sustainable borylation reaction of aliphatic and aromatic halides has been performed. We have also examined the effect of microwave (MW) radiation in the preparation of these type of materials using sustainable graphite nanoplatelets (GNP) as a support. A detailed analysis of all the possible species in solution revealed that the catalysis is mainly due to an interesting synergetic Cu2O/graphene performance, which has been corroborated by an extensive theoretical study. We demonstrated through DFT calculations at a high level of theory that graphene enhances the reactivity of the metal in Cu2O against the halide derivative favoring a radical departure from the halogen. Moreover, this material is able to stabilize radical intermediates providing unexpected pathways not observed using homogeneous Cu(i) catalysed reactions. Finally, we proved that other common carbon-based supports like carbon black, graphene oxide and reduced graphene oxide provided poorer results in the borylation process.
Catalytic Boration of Alkyl Halides with Borane without Hydrodehalogenation Enabled by Titanium Catalyst
Wang, Xianjin,Cui, Penglei,Xia, Chungu,Wu, Lipeng
supporting information, p. 12298 - 12303 (2021/05/07)
An unprecedented and general titanium-catalyzed boration of alkyl (pseudo)halides (alkyl-X, X=I, Br, Cl, OMs) with borane (HBpin, HBcat) is reported. The use of titanium catalyst can successfully suppress the undesired hydrodehalogenation products that prevail using other transition-metal catalysts. A series of synthetically useful alkyl boronate esters are readily obtained from various (primary, secondary, and tertiary) alkyl electrophiles, including unactivated alkyl chlorides, with tolerance of other reducing functional groups such as ester, alkene, and carbamate. Preliminary studies on the mechanism revealed a possible radical reaction pathway. Further extension of our strategy to aryl bromides is also demonstrated.
