Aerobic oxidation of pinacol by vanadium(V) dipicolinate complexes: Evidence for reduction to vanadium(III)

Susan K. Hanson; R. Tom Baker; John C. Gordon; Brian L. Scott; Andrew D. Sutton; David L. Thorn

doi:10.1021/ja807522n

Aerobic oxidation of pinacol by vanadium(V) dipicolinate complexes: Evidence for reduction to vanadium(III)

Susan K. Hanson, R. Tom Baker, John C. Gordon, Brian L. Scott, Andrew D. Sutton, David L. Thorn

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

111 Scopus citations

Abstract

The reactivity of vanadium complexes bearing the ligand dipicolinic acid (H2dipic) with alcohols has been explored. Dipic vanadium complexes are able to catalyze the aerobic oxidative C-C bond cleavage of pinacol. Reaction under anaerobic conditions allowed for isolation of a VIII μ-oxo dimer, supporting the involvement of V ^III in aerobic oxidation reactions. Stoichiometric oxidation of unactivated aliphatic alcohols has also been observed, with oxidation of cyclobutanol producing cyclobutanone in 93% yield. The absence of ringopening products in this reaction provides further support for the involvement of V ^III intermediates.

Original language	English
Pages (from-to)	428-429
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	131
Issue number	2
DOIs	https://doi.org/10.1021/ja807522n
State	Published - Jan 21 2009
Externally published	Yes

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title = "Aerobic oxidation of pinacol by vanadium(V) dipicolinate complexes: Evidence for reduction to vanadium(III)",

abstract = "The reactivity of vanadium complexes bearing the ligand dipicolinic acid (H2dipic) with alcohols has been explored. Dipic vanadium complexes are able to catalyze the aerobic oxidative C-C bond cleavage of pinacol. Reaction under anaerobic conditions allowed for isolation of a VIII μ-oxo dimer, supporting the involvement of V III in aerobic oxidation reactions. Stoichiometric oxidation of unactivated aliphatic alcohols has also been observed, with oxidation of cyclobutanol producing cyclobutanone in 93\% yield. The absence of ringopening products in this reaction provides further support for the involvement of V III intermediates.",

author = "Hanson, \{Susan K.\} and \{Tom Baker\}, R. and Gordon, \{John C.\} and Scott, \{Brian L.\} and Sutton, \{Andrew D.\} and Thorn, \{David L.\}",

year = "2009",

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T1 - Aerobic oxidation of pinacol by vanadium(V) dipicolinate complexes

T2 - Evidence for reduction to vanadium(III)

AU - Hanson, Susan K.

AU - Tom Baker, R.

AU - Gordon, John C.

AU - Scott, Brian L.

AU - Sutton, Andrew D.

AU - Thorn, David L.

PY - 2009/1/21

Y1 - 2009/1/21

N2 - The reactivity of vanadium complexes bearing the ligand dipicolinic acid (H2dipic) with alcohols has been explored. Dipic vanadium complexes are able to catalyze the aerobic oxidative C-C bond cleavage of pinacol. Reaction under anaerobic conditions allowed for isolation of a VIII μ-oxo dimer, supporting the involvement of V III in aerobic oxidation reactions. Stoichiometric oxidation of unactivated aliphatic alcohols has also been observed, with oxidation of cyclobutanol producing cyclobutanone in 93% yield. The absence of ringopening products in this reaction provides further support for the involvement of V III intermediates.

AB - The reactivity of vanadium complexes bearing the ligand dipicolinic acid (H2dipic) with alcohols has been explored. Dipic vanadium complexes are able to catalyze the aerobic oxidative C-C bond cleavage of pinacol. Reaction under anaerobic conditions allowed for isolation of a VIII μ-oxo dimer, supporting the involvement of V III in aerobic oxidation reactions. Stoichiometric oxidation of unactivated aliphatic alcohols has also been observed, with oxidation of cyclobutanol producing cyclobutanone in 93% yield. The absence of ringopening products in this reaction provides further support for the involvement of V III intermediates.

UR - https://www.scopus.com/pages/publications/62849119772

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DO - 10.1021/ja807522n

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 2

ER -

Aerobic oxidation of pinacol by vanadium(V) dipicolinate complexes: Evidence for reduction to vanadium(III)

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