Ortho-Selective Hydrogen Isotope Exchange of Phenols and Benzyl Alcohols by Mesoionic Carbene-Iridium Catalyst

• DOI: 10.1021/acs.orglett.1c03685
• Publication Date: 2021-11-18T16:47:59Z
• Authors: Liang-Liang Zhao; Yixin Wu; Shiqing Huang; Zengyu Zhang; Wei Liu; Xiaoyu Yan
• Keywords: mesoionic carbene; Evolutionary Biology; Ecology; Chemical Sciences not elsewhere classified; Physiology; Biophysics; high ortho selectivity; hydrogen bonding; Biochemistry; iridium catalyst; benzyl alcohols; 01 natural sciences; hydroxyl group; ortho selectivity; 0104 chemical sciences; control experiments indicated; Molecular Biology; sphere direction; Neuroscience; Biotechnology

Hydrogen isotope exchange reactions of phenols and benzyl alcohols have been achieved by a mesoionic carbene-iridium catalyst with high ortho selectivity and high functional group tolerance. Control experiments indicated that acetate is crucial to realize the ortho selectivity, whereas density functional theory calculations supported an outer-sphere direction with hydrogen bonding between acetate and the hydroxyl group.