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<title>UTas ePrints - Reactivity and Mechanism in Oxidative Addition to Palladium(II) and Reductive Ellmlnation from Palladium(IV) and an Estimate of the Palladium-Methyl Bond Energy</title>
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<meta content="Byers, P.K." name="eprints.creators_name" />
<meta content="Canty, A.J." name="eprints.creators_name" />
<meta content="Crespo, M." name="eprints.creators_name" />
<meta content="Puddephatt, R.J." name="eprints.creators_name" />
<meta content="Scott, J.D." name="eprints.creators_name" />
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<meta content="allan.canty@utas.edu.au" name="eprints.creators_id" />
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<meta content="Reactivity and Mechanism in Oxidative Addition to
Palladium(II) and Reductive Ellmlnation from Palladium(IV)
and an Estimate of the Palladium-Methyl Bond Energy" name="eprints.title" />
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<meta content="Oxidative addition of methyl iodide to [PdMe2(bpy)]( bpy = 2,2'-bipyridine) occurs by the SN2 mechanism. Evidence
includes the observation of second-order kinetics in acetone solvent, with a large negative value for the
entropy of activation, and the observation of a cationic species, [PdMe3(bpy)(CD3CN)]+ in, CD3CN solvent. The reaction occurs more slowly than the analogous reaction of [PtMe2(bpy)], but the same mechanism operates. Reductive elimination from [PdIMe3(bpy)] to give ethane and [PdIMe(bpy)] follows good first order kinetics, occurs more rapidly in polar solvents, and is strongly retarded by added iodide. These observations are interpreted in terms of a mechanism that involves preliminary ionization of iodide followed by reductive elimination from the cation [PdMe3(bpy)]+. Studies by differential scanning calorimetry allow an estimate of the Pd-C bond energy of -130 kJ mo1-l to be obtained, and this value is considerably higher than the activation energy for reductive elimination of ethane from [PdIMe3(bpy)]. The reductive elimination step is therefore concerted, and possible mechanisms, which may involve direct C-C coupling or C-C coupling after an agostic CHPd interaction, are discussed. This work is relevant to catalytic C-C coupling reactions using palladium complex catalysts" name="eprints.abstract" />
<meta content="1988" name="eprints.date" />
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<meta content="Byers, P.K. and Canty, A.J. and Crespo, M. and Puddephatt, R.J. and Scott, J.D. (1988) Reactivity and Mechanism in Oxidative Addition to Palladium(II) and Reductive Ellmlnation from Palladium(IV) and an Estimate of the Palladium-Methyl Bond Energy. Organometallics, 7 (6). pp. 1363-1367. ISSN 0276-7333" name="eprints.citation" />
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Palladium(II) and Reductive Ellmlnation from Palladium(IV)
and an Estimate of the Palladium-Methyl Bond Energy" name="DC.title" />
<meta content="Byers, P.K." name="DC.creator" />
<meta content="Canty, A.J." name="DC.creator" />
<meta content="Crespo, M." name="DC.creator" />
<meta content="Puddephatt, R.J." name="DC.creator" />
<meta content="Scott, J.D." name="DC.creator" />
<meta content="259901 Organometallic Chemistry" name="DC.subject" />
<meta content="Oxidative addition of methyl iodide to [PdMe2(bpy)]( bpy = 2,2'-bipyridine) occurs by the SN2 mechanism. Evidence
includes the observation of second-order kinetics in acetone solvent, with a large negative value for the
entropy of activation, and the observation of a cationic species, [PdMe3(bpy)(CD3CN)]+ in, CD3CN solvent. The reaction occurs more slowly than the analogous reaction of [PtMe2(bpy)], but the same mechanism operates. Reductive elimination from [PdIMe3(bpy)] to give ethane and [PdIMe(bpy)] follows good first order kinetics, occurs more rapidly in polar solvents, and is strongly retarded by added iodide. These observations are interpreted in terms of a mechanism that involves preliminary ionization of iodide followed by reductive elimination from the cation [PdMe3(bpy)]+. Studies by differential scanning calorimetry allow an estimate of the Pd-C bond energy of -130 kJ mo1-l to be obtained, and this value is considerably higher than the activation energy for reductive elimination of ethane from [PdIMe3(bpy)]. The reductive elimination step is therefore concerted, and possible mechanisms, which may involve direct C-C coupling or C-C coupling after an agostic CHPd interaction, are discussed. This work is relevant to catalytic C-C coupling reactions using palladium complex catalysts" name="DC.description" />
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<meta content="Byers, P.K. and Canty, A.J. and Crespo, M. and Puddephatt, R.J. and Scott, J.D. (1988) Reactivity and Mechanism in Oxidative Addition to Palladium(II) and Reductive Ellmlnation from Palladium(IV) and an Estimate of the Palladium-Methyl Bond Energy. Organometallics, 7 (6). pp. 1363-1367. ISSN 0276-7333" name="DC.identifier" />
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<h1 class="ep_tm_pagetitle">Reactivity and Mechanism in Oxidative Addition to Palladium(II) and Reductive Ellmlnation from Palladium(IV) and an Estimate of the Palladium-Methyl Bond Energy</h1>
<p style="margin-bottom: 1em" class="not_ep_block"><span class="person_name">Byers, P.K.</span> and <span class="person_name">Canty, A.J.</span> and <span class="person_name">Crespo, M.</span> and <span class="person_name">Puddephatt, R.J.</span> and <span class="person_name">Scott, J.D.</span> (1988) <xhtml:em>Reactivity and Mechanism in Oxidative Addition to Palladium(II) and Reductive Ellmlnation from Palladium(IV) and an Estimate of the Palladium-Methyl Bond Energy.</xhtml:em> Organometallics, 7 (6). pp. 1363-1367. ISSN 0276-7333</p><p style="margin-bottom: 1em" class="not_ep_block"></p><table style="margin-bottom: 1em" class="not_ep_block"><tr><td valign="top" style="text-align:center"><a href="http://eprints.utas.edu.au/2895/1/Organomet1988_2C_1363.pdf"><img alt="[img]" src="http://eprints.utas.edu.au/style/images/fileicons/application_pdf.png" border="0" class="ep_doc_icon" /></a></td><td valign="top"><a href="http://eprints.utas.edu.au/2895/1/Organomet1988_2C_1363.pdf"><span class="ep_document_citation">PDF</span></a> - Full text restricted - Requires a PDF viewer<br />635Kb</td><td><form method="get" accept-charset="utf-8" action="http://eprints.utas.edu.au/cgi/request_doc"><input value="4182" name="docid" accept-charset="utf-8" type="hidden" /><div class=""><input value="Request a copy" name="_action_null" class="ep_form_action_button" onclick="return EPJS_button_pushed( '_action_null' )" type="submit" /> </div></form></td></tr></table><p style="margin-bottom: 1em" class="not_ep_block">Official URL: <a href="http://dx.doi.org/10.1021/om00096a021">http://dx.doi.org/10.1021/om00096a021</a></p><div class="not_ep_block"><h2>Abstract</h2><p style="padding-bottom: 16px; text-align: left; margin: 1em auto 0em auto">Oxidative addition of methyl iodide to [PdMe2(bpy)]( bpy = 2,2'-bipyridine) occurs by the SN2 mechanism. Evidence
includes the observation of second-order kinetics in acetone solvent, with a large negative value for the
entropy of activation, and the observation of a cationic species, [PdMe3(bpy)(CD3CN)]+ in, CD3CN solvent. The reaction occurs more slowly than the analogous reaction of [PtMe2(bpy)], but the same mechanism operates. Reductive elimination from [PdIMe3(bpy)] to give ethane and [PdIMe(bpy)] follows good first order kinetics, occurs more rapidly in polar solvents, and is strongly retarded by added iodide. These observations are interpreted in terms of a mechanism that involves preliminary ionization of iodide followed by reductive elimination from the cation [PdMe3(bpy)]+. Studies by differential scanning calorimetry allow an estimate of the Pd-C bond energy of -130 kJ mo1-l to be obtained, and this value is considerably higher than the activation energy for reductive elimination of ethane from [PdIMe3(bpy)]. The reductive elimination step is therefore concerted, and possible mechanisms, which may involve direct C-C coupling or C-C coupling after an agostic CHPd interaction, are discussed. This work is relevant to catalytic C-C coupling reactions using palladium complex catalysts</p></div><table style="margin-bottom: 1em" border="0" cellpadding="3" class="not_ep_block"><tr><th valign="top" class="ep_row">Item Type:</th><td valign="top" class="ep_row">Article</td></tr><tr><th valign="top" class="ep_row">Subjects:</th><td valign="top" class="ep_row"><a href="http://eprints.utas.edu.au/view/subjects/259901.html">250000 Chemical Sciences > 259900 Other Chemical Sciences > 259901 Organometallic Chemistry</a></td></tr><tr><th valign="top" class="ep_row">Collections:</th><td valign="top" class="ep_row">UNSPECIFIED</td></tr><tr><th valign="top" class="ep_row">ID Code:</th><td valign="top" class="ep_row">2895</td></tr><tr><th valign="top" class="ep_row">Deposited By:</th><td valign="top" class="ep_row"><span class="ep_name_citation"><span class="person_name">Prof Allan J Canty</span></span></td></tr><tr><th valign="top" class="ep_row">Deposited On:</th><td valign="top" class="ep_row">18 Jan 2008 08:49</td></tr><tr><th valign="top" class="ep_row">Last Modified:</th><td valign="top" class="ep_row">18 Jan 2008 08:49</td></tr><tr><th valign="top" class="ep_row">ePrint Statistics:</th><td valign="top" class="ep_row"><a target="ePrintStats" href="/es/index.php?action=show_detail_eprint;id=2895;">View statistics for this ePrint</a></td></tr></table><p align="right">Repository Staff Only: <a href="http://eprints.utas.edu.au/cgi/users/home?screen=EPrint::View&eprintid=2895">item control page</a></p>
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