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On the Gold‐Catalyzed Intramolecular 7‐ exo‐trig Hydroamination of Allenes
Author(s) -
Pflästerer Daniel,
Dolbundalchok Praphasiri,
Rafique Shahid,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300154
Subject(s) - hydroamination , chemistry , allene , aniline , nucleophile , isomerization , intramolecular force , catalysis , diene , medicinal chemistry , photochemistry , stereochemistry , organic chemistry , natural rubber
Abstract Aniline derivatives with allene side tethers were tested as substrates for a gold‐catalyzed 7‐ exo‐trig hydroamination reaction. The nucleophilicity of the aniline derivatives plays an important role for the outcome of the reaction. While electron‐deficient protecting groups at the nitrogen led to competing pathways like hydroarylation or an allene to diene isomerization, clean formation of the desired benzoxazepines was obtained with unprotected aniline derivatives.