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Title: Selective C-H Functionalization of Methane and Ethane by a Molecular Sb V Complex

Journal Article · · Angewandte Chemie (International Edition)
 [1];  [1];  [2];  [1];  [3];  [2]; ORCiD logo [3];  [1]
  1. Scripps Research Inst., Jupiter, FL (United States)
  2. Hyconix Incorp., Chicago, IL (United States)
  3. Brigham Young Univ., Provo, UT (United States)
+ Show Author Affiliations

Owing to the strong nonpolar bonds involved, selective C-H functionalization of methane and ethane to esters remains a challenge for molecular homogeneous chemistry. Here, we report that the computationally predicted main-group p-block SbV (TFA)5 complex selectively functionalizes the C-H bonds of methane and ethane to the corresponding mono and/or diol trifluoroacetate esters at 110-180 °C with yields for ethane of up to 60 % with over 90 % selectivity. Additionally, experimental and computational studies support a unique mechanism that involves SbV -mediated C-H activation followed by functionalization of a SbV -alkyl intermediate.

Research Organization:
Brigham Young Univ., Provo, UT (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division
Grant/Contract Number:
SC0018329
OSTI ID:
1595925
Alternate ID(s):
OSTI ID: 1491423
Journal Information:
Angewandte Chemie (International Edition), Vol. 58, Issue 8; ISSN 1433-7851
Publisher:
WileyCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 15 works
Citation information provided by
Web of Science

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Cited By (4)

Selective Photo‐Oxygenation of Light Alkanes Using Iodine Oxides and Chloride journal September 2019
From a 1D Sb Coordination Polymer to a 3D Sb Framework with Pyrazine: Switching off the Stereochemically Active Lone-Pair: From a 1D Sb Coordination Polymer to a 3D Sb Framework with Pyrazine: Switching off the Stereochemically Active Lone-Pair journal May 2020
Establishing the correlation between catalytic performance and N→Sb donor–acceptor interaction: systematic assessment of azastibocine halide derivatives as water tolerant Lewis acids journal January 2019
Unveiling the potential of scandium complexes for methane C–H bond activation: a computational study journal January 2019

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
alkanes
antimony
C−H activation
main-group metals
oxidation