Selectivity modulation of the Ley–Griffith TPAP oxidation with N-Oxide salts

Peter W. Moore; Yanxiao Jiao; Paul M. Mirzayans; Lexter Ng Qi Sheng; Jordan P. Hooker; Craig M. Williams

doi:10.1002/ejoc.201600453

Selectivity modulation of the Ley–Griffith TPAP oxidation with N-Oxide salts

Peter W. Moore, Yanxiao Jiao, Paul M. Mirzayans, Lexter Ng Qi Sheng, Jordan P. Hooker, Craig M. Williams

Research output: Contribution to journal › Article › Research › peer-review

14 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3401-3407
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	20
DOIs	https://doi.org/10.1002/ejoc.201600453
Publication status	Published - Jul 2016
Externally published	Yes

Keywords

Alcohols
Aldehydes
Ley-Griffith reaction
N-Oxide salts
Oxidation
TPAP

Access to Document

10.1002/ejoc.201600453

Cite this

@article{aa566d23846944c08e7388c240809670,

title = "Selectivity modulation of the Ley–Griffith TPAP oxidation with N-Oxide salts",

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.",

keywords = "Alcohols, Aldehydes, Ley-Griffith reaction, N-Oxide salts, Oxidation, TPAP",

author = "Moore, \{Peter W.\} and Yanxiao Jiao and Mirzayans, \{Paul M.\} and Sheng, \{Lexter Ng Qi\} and Hooker, \{Jordan P.\} and Williams, \{Craig M.\}",

note = "Funding Information: We thank the University of Queensland (UQ) for financial support and Prof. Paul Bernhardt for collecting X-ray crystallographic data. In addition, Y. J. gratefully acknowledges the Department of Education, Guangxi Zhuang Autonomous Region, China, for a study-abroad funding. The Australian Research Council, for a Future Fellowship award (FT110100851) to C. M. W. and project funding (DP160102887), is also gratefully acknowledged. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2016",

month = jul,

doi = "10.1002/ejoc.201600453",

language = "English",

volume = "2016",

pages = "3401--3407",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-Blackwell",

number = "20",

}

TY - JOUR

T1 - Selectivity modulation of the Ley–Griffith TPAP oxidation with N-Oxide salts

AU - Moore, Peter W.

AU - Jiao, Yanxiao

AU - Mirzayans, Paul M.

AU - Sheng, Lexter Ng Qi

AU - Hooker, Jordan P.

AU - Williams, Craig M.

N1 - Funding Information: We thank the University of Queensland (UQ) for financial support and Prof. Paul Bernhardt for collecting X-ray crystallographic data. In addition, Y. J. gratefully acknowledges the Department of Education, Guangxi Zhuang Autonomous Region, China, for a study-abroad funding. The Australian Research Council, for a Future Fellowship award (FT110100851) to C. M. W. and project funding (DP160102887), is also gratefully acknowledged. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2016/7

Y1 - 2016/7

N2 - 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.

AB - 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.

KW - Alcohols

KW - Aldehydes

KW - Ley-Griffith reaction

KW - N-Oxide salts

KW - Oxidation

KW - TPAP

UR - https://www.scopus.com/pages/publications/84976867118

U2 - 10.1002/ejoc.201600453

DO - 10.1002/ejoc.201600453

M3 - Article

AN - SCOPUS:84976867118

SN - 1434-193X

VL - 2016

SP - 3401

EP - 3407

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 20

ER -

Selectivity modulation of the Ley–Griffith TPAP oxidation with N-Oxide salts

Abstract

Keywords

Access to Document

Other files and links

Cite this