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Making Carbon–Chlorine Bonds by Dipalladium Electrocatalysis

Durrell, Alec C. and Jackson, Megan N. and Hazari, Nilay and Gray, Harry B. (2013) Making Carbon–Chlorine Bonds by Dipalladium Electrocatalysis. European Journal of Inorganic Chemistry, 2013 (7). pp. 1134-1137. ISSN 1434-1948. http://resolver.caltech.edu/CaltechAUTHORS:20130507-103535110

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Abstract

[(Benzo[h]quinolinyl)Pd^(II)(μ-OAc)]_2 and [(2-phenylpyridinyl)PdII(μ-OAc)]_2 undergo one-electron oxidation to afford mixed-valent (Pd^(II)–Pd^(III)) species. Electrochemical oxidation of the Pd^(II)–Pd^(II) complexes in the presence of chloride at the Pd^(III)–Pd^(II)/Pd^(II)–Pd^(II) potential results in a two-electron loss with addition of two chlorides to form [(benzo[h]quinolinyl)Pd^(III)Cl(μ-OAc)]_2 and [(2-phenylpyridinyl)Pd^(III)Cl(μ-OAc)]_2, respectively. When both excess benzo[h]quinoline and chloride are present, [(benzo[h]quinolinyl)Pd^(II)(μ-OAc)]2 electrocatalyzes the chlorination of the substrate to afford 10-chlorobenzo[h]quinoline with high chemical and Faradaic yields.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/ejic.201201498DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/ejic.201201498/abstractPublisherArticle
Additional Information:© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: December 11, 2012; Published Online: January 18, 2013. This work was supported by an National Science Foundation (NSF) Center for Innovation (CCI Solar, CHE-0802907), the Amgen Foundation (M. N. J.), and the Caltech Summer Undergraduate Research Fellowship Program (M. N. J.).
Group:CCI Solar Fuels
Funders:
Funding AgencyGrant Number
NSF Center for InnovationCHE-0802907
Amgen FoundationUNSPECIFIED
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
Subject Keywords:Palladium; Electrochemistry; C–H activation; C–Cl bond formation
Record Number:CaltechAUTHORS:20130507-103535110
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20130507-103535110
Official Citation:Durrell, A. C., Jackson, M. N., Hazari, N. and Gray, H. B. (2013), Making Carbon–Chlorine Bonds by Dipalladium Electrocatalysis. Eur. J. Inorg. Chem., 2013: 1134–1137. doi: 10.1002/ejic.201201498
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:38320
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:07 May 2013 18:41
Last Modified:04 Apr 2014 02:12

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