Selectivity Modulation of the Ley–Griffith TPAP Oxidation with N‐Oxide Salts. Issue 20 (27th June 2016)

• Record Type: Journal Article
• Authors: Moore, Peter W.; Jiao, Yanxiao; Mirzayans, Paul M.; Sheng, Lexter Ng Qi; Hooker, Jordan P.; Williams, Craig M.
• Is Part Of: European journal of organic chemistry. Issue 20(2016)
• Page Start: 3401
• Page End: 3407
• Publication Date: 2016-06-27
• Subjects: Alcohols -- Oxidation -- Aldehydes -- Ley‐Griffith reaction -- N‐Oxide salts -- TPAP; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600453
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : 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.