title: Why does Togni's reagent I exist in the high-energy hypervalent iodine form? Re-evaluation of benziodoxole based hypervalent iodine reagents.
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.
authors.affiliation: Lab of Computational Chemistry and Drug Design, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China. zhangxh@pkusz.edu.cn and Center for Computational Quantum Chemistry, University of Georgia, Athens, GA 30602, USA. qc@uga.edu.
authors.forename: Tian-Yu
authors.initials: TY
authors.lastname: Sun
authors.affiliation: Center for Computational Quantum Chemistry, University of Georgia, Athens, GA 30602, USA. qc@uga.edu.
authors.forename: Xiao
authors.initials: X
authors.lastname: Wang
authors.affiliation: Lab of Computational Chemistry and Drug Design, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China. zhangxh@pkusz.edu.cn.
authors.forename: Hao
authors.initials: H
authors.lastname: Geng
authors.affiliation: Center for Computational Quantum Chemistry, University of Georgia, Athens, GA 30602, USA. qc@uga.edu.
authors.forename: Yaoming
authors.initials: Y
authors.lastname: Xie
authors.affiliation: Lab of Computational Chemistry and Drug Design, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China. zhangxh@pkusz.edu.cn and College of Chemistry, Peking University, Beijing 100871, China.
authors.forename: Yun-Dong
authors.initials: YD
authors.lastname: Wu
authors.affiliation: Lab of Computational Chemistry and Drug Design, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China. zhangxh@pkusz.edu.cn.
authors.forename: Xinhao
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Center for Computational Quantum Chemistry, University of Georgia, Athens, GA 30602, USA. qc@uga.edu.
authors.forename: Henry F
authors.initials: HF
authors.lastname: Schaefer