Functionalization of rhenium aryl bonds by O-atom transfer

Steven M. Bischof; Mu Jeng Cheng; Robert J. Nielsen; T. Brent Gunnoe; William A. Goddard; Roy A. Periana

doi:10.1021/om2002365

Functionalization of rhenium aryl bonds by O-atom transfer

Steven M. Bischof
, Mu Jeng Cheng
, Robert J. Nielsen
, T. Brent Gunnoe
, William A. Goddard
, Roy A. Periana

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

Abstract

Aryltrioxorhenium (ArReO₃) has been demonstrated to show rapid oxy-functionalization upon reaction with O-atom donors, YO, to selectively generate the corresponding phenols in near quantitative yields. ¹⁸O-Labeling experiments show that the oxygen in the products is exclusively from YO. DFT studies reveal a 10.7 kcal/mol barrier (Ar = Ph) for oxy-functionalization with H₂O₂ via a Baeyer-Villiger type mechanism involving nucleophilic attack of the aryl group on an electrophilic oxygen of YO coordinated to rhenium.

Original language	English
Pages (from-to)	2079-2082
Number of pages	4
Journal	Organometallics
Volume	30
Issue number	8
DOIs	https://doi.org/10.1021/om2002365
Publication status	Published - 25 Apr 2011
Externally published	Yes

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title = "Functionalization of rhenium aryl bonds by O-atom transfer",

abstract = "Aryltrioxorhenium (ArReO3) has been demonstrated to show rapid oxy-functionalization upon reaction with O-atom donors, YO, to selectively generate the corresponding phenols in near quantitative yields. 18O-Labeling experiments show that the oxygen in the products is exclusively from YO. DFT studies reveal a 10.7 kcal/mol barrier (Ar = Ph) for oxy-functionalization with H2O2 via a Baeyer-Villiger type mechanism involving nucleophilic attack of the aryl group on an electrophilic oxygen of YO coordinated to rhenium.",

author = "Bischof, \{Steven M.\} and Cheng, \{Mu Jeng\} and Nielsen, \{Robert J.\} and Gunnoe, \{T. Brent\} and Goddard, \{William A.\} and Periana, \{Roy A.\}",

year = "2011",

month = apr,

day = "25",

doi = "10.1021/om2002365",

language = "English",

volume = "30",

pages = "2079--2082",

journal = "Organometallics",

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T1 - Functionalization of rhenium aryl bonds by O-atom transfer

AU - Bischof, Steven M.

AU - Cheng, Mu Jeng

AU - Nielsen, Robert J.

AU - Gunnoe, T. Brent

AU - Goddard, William A.

AU - Periana, Roy A.

PY - 2011/4/25

Y1 - 2011/4/25

N2 - Aryltrioxorhenium (ArReO3) has been demonstrated to show rapid oxy-functionalization upon reaction with O-atom donors, YO, to selectively generate the corresponding phenols in near quantitative yields. 18O-Labeling experiments show that the oxygen in the products is exclusively from YO. DFT studies reveal a 10.7 kcal/mol barrier (Ar = Ph) for oxy-functionalization with H2O2 via a Baeyer-Villiger type mechanism involving nucleophilic attack of the aryl group on an electrophilic oxygen of YO coordinated to rhenium.

AB - Aryltrioxorhenium (ArReO3) has been demonstrated to show rapid oxy-functionalization upon reaction with O-atom donors, YO, to selectively generate the corresponding phenols in near quantitative yields. 18O-Labeling experiments show that the oxygen in the products is exclusively from YO. DFT studies reveal a 10.7 kcal/mol barrier (Ar = Ph) for oxy-functionalization with H2O2 via a Baeyer-Villiger type mechanism involving nucleophilic attack of the aryl group on an electrophilic oxygen of YO coordinated to rhenium.

UR - https://www.scopus.com/pages/publications/79954507334

U2 - 10.1021/om2002365

DO - 10.1021/om2002365

M3 - Article

AN - SCOPUS:79954507334

SN - 0276-7333

VL - 30

SP - 2079

EP - 2082

JO - Organometallics

JF - Organometallics

IS - 8

ER -

Functionalization of rhenium aryl bonds by O-atom transfer

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