Redox-triggered cascade dearomative cyclizations enabled by hexafluoroisopropanol

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...

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Published inChemical 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
LanguageEnglish
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
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Summary: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 sequence. This unique transformation addressed the drawbacks of hydride transfer-involved redox-neutral reactions.
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ISSN:2041-6520
2041-6539
DOI:10.1039/C8SC03339K