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Formal Aniline Synthesis from Phenols through Deoxygenative N‐Centered Radical Substitution
Author(s) -
Lardy Samuel W.,
Luong Kristine C.,
Schmidt Valerie A.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904288
Subject(s) - aniline , phenols , chemistry , phenol , lignin , steric effects , organic chemistry , radical
Phenolic, lignin‐derived substrates have emerged as desirable biorenewable chemical feedstocks for coupling reactions. A radical‐mediated conversion of phenol derivatives to anilines is reported, using unfunctionalized hydroxamic acids as the N‐centered radical source. The applicability of this triethyl phosphite mediated O‐atom transfer approach, which tolerates a range of steric and electronic demands to naturally occurring phenols and lignin models, has been demonstrated in this work to access the corresponding aniline derivatives.