Synthesis and Reactivity of Cationic Palladium Phosphine Carboxylate ComplexesClick to copy article linkArticle link copied!
Abstract
Simple routes to two new types of mononuclear cationic palladium phosphine acetate complexes featuring κ1- or κ2-carboxylates have been developed, and the resulting materials have been characterized by single-crystal X-ray diffraction. In acetonitrile the complex [(iPr3P)2Pd(κ2O,O‘-OAc)]+ leads not to the independently prepared trans-[(iPr3P)2Pd(MeCN)(OAc)]+ but to reversible cyclometalation to form [(iPr3P)(MeCN)Pd(κ2C,P-C(Me)2PiPr2)]+.
†
Case Western Reserve University.
‡
Current address: Department of Chemistry, University of Delhi, Delhi 110 007, India.
§
Promerus LLC.
*
In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.
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(2)
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(13)
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(23)
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(1)
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(19)
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(6)
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(2)
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(6)
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