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Selectivity Modulation of the Ley–Griffith TPAP Oxidation with N ‐Oxide Salts
Author(s) -
Moore Peter W.,
Jiao Yanxiao,
Mirzayans Paul M.,
Sheng Lexter Ng Qi,
Hooker Jordan P.,
Williams Craig M.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600453
Subject(s) - tetraphenylborate , chemistry , salt (chemistry) , anhydrous , oxide , crystallization , selectivity , sodium tetraphenylborate , medicinal chemistry , allylic rearrangement , inorganic chemistry , organic chemistry , nuclear chemistry , catalysis , ion
A wide variety of novel non‐hygroscopic N ‐oxide tetraphenylborate salts were synthesized and evaluated as co‐oxidants in the Ley–Griffith (TPAP) oxidation of benzylic and allylic alcohols under non‐anhydrous conditions. The novel DABCOO · TPB (2:1) salt was herein unearthed as a viable competitor to the first‐generation NMO · TPB (2:1) salt, but more importantly gave increased performance under oxidative competition. X‐ray crystal structure analysis and NMR spectroscopy revealed that depending on the crystallization conditions 1:1, 2:1 or 3:2 N ‐oxide–tetraphenylborate salts could be formed.