Selectivity Modulation of the Ley-Griffith TPAP Oxidation with N-Oxide Salts

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 t...

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Bibliographic Details
Published in:European journal of organic chemistry 2016-07, Vol.2016 (20), p.3401-3407
Main Authors: Moore, Peter W., Jiao, Yanxiao, Mirzayans, Paul M., Sheng, Lexter Ng Qi, Hooker, Jordan P., Williams, Craig M.
Format: Article
Language:English
Subjects:
Alcohols
Aldehydes
Ley-Griffith reaction
N-Oxide salts
Oxidation
TPAP
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Summary: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. Under non‐anhydrous conditions novel N‐oxide tetraphenylborate salts act as co‐oxidants in the Ley–Griffith (TPAP) oxidation of benzylic and allylic alcohols. Specifically, the DABCOO·TPB salt was found to give increased performance under oxidative competition.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600453