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Designing non-​innocent ligands for multiproton-​multielectron chemistry: Reactivity of Pd-​hydroquinone complexes

Horak, Kyle T. and Agapie, Theodor (2014) Designing non-​innocent ligands for multiproton-​multielectron chemistry: Reactivity of Pd-​hydroquinone complexes. In: 248th American Chemical Society National Meeting & Exposition, August 10-14, 2014, San Francisco, CA. http://resolver.caltech.edu/CaltechAUTHORS:20140812-142635226

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Abstract

The use of redox-active and non-innocent ligand frameworks has been shown to expand or improve the reactivity and catalytic behavior of transition metal complexes. While ligands capable of storing electrons or protons are well precedented few have been shown to shuttle both protons and electrons to and from the metal center. A ligand framework capable of facilitating multiple proton and electron transfers was targeted. A para-terphenyl diphosphine ligand contg. a redox-active hydroquinone moiety was successfully synthesized. Metalation with M(OAc)_2 (M = Ni, Pd) readily afforded the reduced zero-valent metal center coordinated to the quinone form of the ligand. A Pd(0)-hydroquinone complex was synthesized and found to readily reduce a variety of substrates, including dioxygen and organoazides, to quant. yield the Pd(0)-quinone complex. A Ag(I)-hydroquinone complex and a Pd(0) complex supported by a redox-inactive para-methoxy substituted central arene were utilized as probes for ligand-only and Pd-only reactivity, resp. The mechanism of substrate activation was studied to analyze the role of the hydroquinone moiety as a two electron and two proton reservoir.


Item Type:Conference or Workshop Item (Paper)
Related URLs:
URLURL TypeDescription
http://www.acs.org/content/acs/en/meetings/fall-2014.htmlOrganizationConference Website
ORCID:
AuthorORCID
Agapie, Theodor0000-0002-9692-7614
Additional Information:© 2014 American Chemical Society.
Record Number:CaltechAUTHORS:20140812-142635226
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20140812-142635226
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:48428
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:12 Aug 2014 21:30
Last Modified:05 May 2017 20:20

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