887757-48-4Relevant 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.
Pd-Catalyzed Site-Selective Borylation of Simple Arenes via Thianthrenation?
Chen, Xiao-Yue,Huang, Yu-Hao,Zhou, Jian,Wang, Peng
, p. 1269 - 1272 (2020/08/13)
Site-selective borylation of simple arenes was realized in one pot via an electrophilic thianthrenation/Pd-catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations, and is suitable for late-stage functionalization of a wide range of pharmaceuticals and complex bioactive molecules.
Exemplifying Prediction of Preferred Coupling Partners in Developing a Buchwald-Hartwig Coupling for the Synthesis of a c-Kit Inhibitor
Wu, Quanbing,Xiong, Xin,Cao, Yudong,He, Lijuan,Fei, Zhongbo
, p. 557 - 561 (2018/04/27)
Two convergent syntheses for compound 1 are described that apply Buchwald-Hartwig coupling as the key step. This development work provides a direct comparison of the coupling results from different coupling partners and illustrates that more efficiency ca
