Borane-Catalyzed Chemoselectivity-Controllable N-Alkylation and <i>ortho</i> C-Alkylation of Unprotected Arylamines Using Benzylic Alcohols
作者:Shan-Shui Meng、Xiaowen Tang、Xiang Luo、Ruibo Wu、Jun-Ling Zhao、Albert S. C. Chan
DOI:10.1021/acscatal.9b03038
日期:2019.9.6
efficient and highlychemoselective alkylation of unprotected arylamines using alcohols catalyzed by B(C6F5)3 has been developed. The reaction gives N-alkylated products and ortho C-alkylated products in different solvents in good chemoselectivities and yields. Control experiments and DFT calculations indicated that the borane underwent alcohol/arylamine exchange to ensure catalytic activity, and a
已经开发出一种空前的方案,用于使用受B(C 6 F 5)3催化的醇对未保护的芳基胺进行高效且高度化学选择性的烷基化反应。该反应在不同溶剂中以良好的化学选择性和收率得到N-烷基化产物和邻C-烷基化产物。控制实验和DFT计算表明,硼烷进行了醇/芳基胺交换以确保催化活性,并提出了涉及碳正离子化的可能机理。
Correction to Photocatalytic and Chemoselective Transfer Hydrogenation of Diarylimines in Batch and Continuous Flow
作者:Dean J. van As、Timothy U. Connell、Martin Brzozowski、Andrew D. Scully、Anastasios Polyzos
DOI:10.1021/acs.orglett.8b02023
日期:2018.7.20
Photocatalytic and Chemoselective Transfer Hydrogenation of Diarylimines in Batch and Continuous Flow
作者:Dean J. van As、Timothy U. Connell、Martin Brzozowski、Andrew D. Scully、Anastasios Polyzos
DOI:10.1021/acs.orglett.7b03565
日期:2018.2.16
imines in batch and continuous flow is described. The reaction utilizes Et3N as both hydrogen source and single-electron donor, enabling the selective reduction of imines derived from diarylketimines containing other reducible functional groups including nitriles, halides, esters, and ketones. The dual role of Et3N was confirmed by fluorescence quenching measurements, transient absorption spectroscopy,