文献类型：期刊文献

英文题名：Lewis Acid-Controlled Regioselective Phosphorylation of 2-Indolylmethanols with Diarylphosphine Oxides: Synthesis of Highly Substituted Indoles

作者：Hu, Chen[1,2];Hong, Gang[3];He, Yuchen[1,2];Zhou, Chen[1,2];Kozlowski, Marisa C.[3];Wang, Limin[1,2]

机构：[1]East China Univ Sci & Technol, Inst Fine Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

年份：2018

卷号：83

期号：8

起止页码：4739

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：;EI(收录号：20181705052258);WOS:【SCI-EXPANDED(收录号:WOS:000430898500040)，CCR-EXPANDED(收录号:WOS:000430898500040)】；

基金：This research was financially supported by the National Nature Science Foundation of China (21772039, 21272069) and the Fundamental Research Funds for the Central Universities and Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, and we thank the Chinese Scholarship Council for financial support. We are grateful to Sergei Tcyrulnikov for molecular orbital calculations and XSEDE (TG-CHE120052) for computational resources.

语种：英文

外文关键词：Ligands - Phosphorylation - Polycyclic aromatic hydrocarbons - Phosphorus compounds - Rare earths

摘要：The Lewis acid-promoted phosphorylation of 2-indolylmethanols with diarylphosphine oxides is described. The regioselectivity of the reaction can be modulated by the choice of rare earth metal Lewis acid, offering a highly selective approach to structurally diverse indole derivatives in up to 97% yield for over 50 examples. This strategy features high selectivity, good functional group tolerance, and easy scalability. The utility of this method is further highlighted by facile modification of the products to access novel indole-based phosphine ligand.