| Title | Why does Togni's reagent I exist in the high-energy hypervalent iodine form? Re-evaluation of benziodoxole based hypervalent iodine reagents |
| Authors | Sun, Tian-Yu Wang, Xiao Geng, Hao Xie, Yaoming Wu, Yun-Dong Zhang, Xinhao Schaefer, Henry F., III |
| Affiliation | Peking Univ, Shenzhen Grad Sch, Lab Computat Chem & Drug Design, Key Lab Chem Genom, Shenzhen 518055, Peoples R China. Univ Georgia, Ctr Computat Quantum Chem, Athens, GA 30602 USA. Peking Univ, Coll Chem, Beijing 100871, Peoples R China. Peking Univ, Shenzhen Grad Sch, Lab Computat Chem & Drug Design, Key Lab Chem Genom, Shenzhen 518055, Peoples R China. Schaefer, HF (reprint author), Univ Georgia, Ctr Computat Quantum Chem, Athens, GA 30602 USA. |
| Keywords | DENSITY-FUNCTIONAL THEORY ELECTROPHILIC TRIFLUOROMETHYLATION TRANS-INFLUENCE CONCERTED MECHANISM REACTIVITY COMPLEXES LIGANDS DFT ELECTRONEGATIVITY ALKYNYLATION |
| Issue Date | 2016 |
| Publisher | CHEMICAL COMMUNICATIONS |
| Citation | CHEMICAL COMMUNICATIONS.2016,52,(31),5371-5374. |
| Abstract | Togni's reagents have become very popular trifluoromethylating reagents in organic synthesis. The existing form of Togni's reagent I is a hypervalent iodine compound which lies much higher in energy than its ether isomer. The high-energy hypervalent iodine form makes Togni's reagent I very effective and versatile. The energy differences between the two forms correlate with the trans influence of the substituents. The five-membered ring in the benziodoxole-based scaffold is an important reason for its existence in the higher-energy form. The relation to Buchwald's 2014 research is discussed. |
| URI | http://hdl.handle.net/20.500.11897/434671 |
| ISSN | 1359-7345 |
| DOI | 10.1039/c6cc00384b |
| Indexed | SCI(E) PubMed |
| Appears in Collections: | 深圳研究生院待认领 å å¦ä¸ å å å·¥ç¨ å¦é ¢ |
