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Pt(pop-BF2) as a photosensitizer in photocatalytic carbon-chlorine bond formation

Jackson, Megan N. and Ener, Maraia E. and Warren, Jeffrey J. and Gray, Harry B. (2013) Pt(pop-BF2) as a photosensitizer in photocatalytic carbon-chlorine bond formation. In: 245th ACS National Meeting & Exposition, Abstracts of Papers, 7-11 April 2013, New Orleans, LA.

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Palladium complexes perform regioselective C-H functionalizations, which are essential for many syntheses. We are interested in halogenation of C-H bonds using [(benzo[h]quinoline)PdII(μ-OAc)]2 catalysts. Bulk electrolysis expts. show that we can chlorinate C-H bonds using chloride and Pd catalysts, eliminating the need for harsh chlorinating agents. To improve the speed and energetic cost of C-H transformations we are exploring reactions with photooxidants. Electronically excited fluoroborated tetrakis(μ-pyrophosphito)diplatinate(II) (Pt(pop-BF2)) undergoes facile electron transfer reactions. Electrochem. (E°(PtII-PtII/PtIPtII) = 1.3 V vs. SCE in MeCN) and fluorescence data were used to calc. E°(*PtII-PtII/PtII-PtI) = 1.4 V vs. SCE, suggesting that electronically excited Pt(pop-BF2) can oxidize Pd catalysts. Absorbance spectra of the transiently reduced Pt complexes were recorded. Time-resolved laser expts. in the presence of Pd catalyst suggest that *Pt(pop-BF2) generates catalytically active Pd intermediates, making it a viable sensitizer for photocatalyic C-H functionalizations.

Item Type:Conference or Workshop Item (Paper)
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URLURL TypeDescription Paper
Warren, Jeffrey J.0000-0002-1747-3029
Gray, Harry B.0000-0002-7937-7876
Additional Information:© 2013 American Chemical Society.
Record Number:CaltechAUTHORS:20130719-081932359
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:39458
Deposited By: Tony Diaz
Deposited On:19 Aug 2013 21:38
Last Modified:27 Feb 2020 00:33

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