Redox-triggered cascade dearomative cyclizations enabled by hexafluoroisopropanol

• Published in: Chemical science (Cambridge) Vol. 9; no. 43; pp. 8253 - 8259
• Main Authors: Li, Shuai-Shuai, Lv, Xintong, Ren, Didi, Shao, Chang-Lun, Liu, Qing, Xiao, Jian
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 21.11.2018; Royal Society of Chemistry
• Subjects: Amines; Chemical industry; Chemistry; Chemistry, Multidisciplinary; Crystallography; Hydrides; Hydrogen bonding; Hydrogen storage; Phenols; Physical Sciences; Science & Technology; C(SP)-H BOND FUNCTIONALIZATION; INTRAMOLECULAR 4+2 CYCLOADDITION; ASYMMETRIC-SYNTHESIS; ORTHO-QUINONE METHIDES; INITIATED CASCADE; C-H FUNCTIONALIZATION; SELECTIVE ACTIVATION; INDOLYL ALCOHOLS; METAL-FREE; HYDRIDE TRANSFER

An unprecedented cascade dearomative cyclization through hydrogen-bonding-assisted hydride transfer is realized. The aggregate effect of HFIP enables the rapid buildup of polycyclic amines directly from phenols and o -aminobenzaldehydes via a cascade dearomatization/rearomatization/dearomatization s...