1232132-73-8Relevant articles and documents
Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds
Arman, Hadi D.,Dang, Hang. T.,Haug, Graham C.,He, Ru,Jin, Shengfei,Larionov, Oleg V.,Nguyen, Viet D.,Nguyen, Vu T.,Schanze, Kirk S.
supporting information, (2020/02/04)
Boronic acids are centrally important functional motifs and synthetic precursors. Visible light-induced borylation may provide access to structurally diverse boronates, but a broadly efficient photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C-O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron-rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reaction exhibits excellent functional group tolerance, as demonstrated by the borylation of a range of structurally complex substrates. Remarkably, the reaction is catalyzed by phenothiazine, a simple organic photocatalyst with MW 200 that mediates the previously unachievable visible light-induced single electron reduction of phenol derivatives with reduction potentials as negative as approximately - 3 V versus SCE by a proton-coupled electron transfer mechanism. Mechanistic studies point to the crucial role of the photocatalyst-base interaction.
Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes
Rzhevskiy, Sergey A.,Topchiy, Maxim A.,Golenko, Yulia D.,Gribanov, Pavel S.,Sterligov, Grigorii K.,Kirilenko, Nikita Yu.,Ageshina, Alexandra A.,Bermeshev, Maxim V.,Nechaev, Mikhail S.,Asachenko, Andrey F.
, p. 569 - 571 (2020/10/09)
Borylation of arenes with bis(pinacolato)diboron catalyzed by sterically encumbered NHC platinum complexes proceeds predominantly at ortho-position even in the absence of a directing group (o: m: p ratio up to 10: 3: 1). The similar borylation with pinacolborane would proceed less selectively.
Synthesis of Amino- and Hydroxymethyl Benzoxaboroles: Prominent Scaffolds for Further Functionalization
Fuscaldo, Rodrigo S.,Vontobel, Pedro H. V.,Boeira, Eduam O.,Moro, Angélica V.,Costa, Jessie S. da
, p. 2050 - 2055 (2019/03/07)
Herein, we describe the development of a short, simple, and efficient synthesis of amino- and hydroxymethyl-substituted benzoxaboroles. The key step in our strategy was the early stage incorporation of the boron by the borylation of an aniline. The formed boronates were then elaborated to the final products in two additional steps, usually in good yields. The synthetic sequence was amenable to be performed on a preparative scale and 4-amino benzoxaborole 4b and 6-hydroxymethyl benzoxaborole 10c have been prepared, without any significant decrease in the overall yield. The amino and hydroxymethyl present at the molecules are useful for further elaboration and/or conjugation to bioactive molecules and therefore we believe that this method should be useful in the development of new compounds for Medicinal Chemistry.
