A New Mode of Reactivity for Pyridine N-Oxide:  C−H Activation with Uranium(IV) and Thorium(IV) Bis(alkyl) Complexes

Uranium(IV) and thorium(IV) bis(alkyl) complexes of the type (C5Me5)2AnR2 (An = U, Th; R = CH3, CH2Ph) activate the sp2 and sp3 hybridized C−H bonds in pyridine N-oxide and lutidine N-oxide to produce the corresponding cyclometalated complexes, (C5Me5)2An(R)[η2-(O,C)-ONC5H4] and (C5Me5)2An(R)[η2-(O,...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-02, Vol.127 (5), p.1338-1339
Main Authors: Pool, Jaime A, Scott, Brian L, Kiplinger, Jaqueline L
Format: Article
Language:English
Subjects:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
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Summary:Uranium(IV) and thorium(IV) bis(alkyl) complexes of the type (C5Me5)2AnR2 (An = U, Th; R = CH3, CH2Ph) activate the sp2 and sp3 hybridized C−H bonds in pyridine N-oxide and lutidine N-oxide to produce the corresponding cyclometalated complexes, (C5Me5)2An(R)[η2-(O,C)-ONC5H4] and (C5Me5)2An(R)[η2-(O,C)-ON-2-CH2-5-CH3-C5H3]. These provide rare examples of C−H activation chemistry mediated by actinide metal centers. This chemistry is in contrast to the known oxygen atom transfer reactivity patterns of pyridine N-oxides with oxophilic metal complexes and constitutes a new mode of reactivity for pyridine N-oxides.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja044153o