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Molecules 2015, 20(7), 12979-12991; doi:10.3390/molecules200712979

Chloro({2-[mesityl(quinolin-8-yl-κN)boryl]-3,5-dimethyl-phenyl}methyl-κC)palladium(II) as a Catalyst for Heck Reactions

Department of Chemistry, University of South Dakota, 414 E. Clark St., Vermillion, SD 57069, USA
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Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 1 May 2015 / Revised: 9 July 2015 / Accepted: 15 July 2015 / Published: 17 July 2015
(This article belongs to the Special Issue The Reactivity of Frustrated Lewis Pairs)
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Abstract

We recently reported an air and moisture stable 16-electron borapalladacycle formed upon combination of 8-quinolyldimesitylborane with bis(benzonitrile)dichloropalladium(II). The complex features a tucked mesityl group formed upon metalation of an ortho-methyl group on a mesityl; however it is unusually stable due to contribution of the boron pz orbital in delocalizing the carbanion that gives rise to an η4-boratabutadiene fragment coordinated to Pd(II), as evidenced from crystallographic data. This complex was observed to be a highly active catalyst for the Heck reaction. Data of the catalyst activity are presented alongside data found in the literature, and initial comparison reveals that the borapalladacycle is quite active. The observed catalysis suggests the borapalladacycle readily undergoes reductive elimination; however the Pd(0) complex has not yet been isolated. Nevertheless, the ambiphilic ligand 8-quinolyldimesitylborane may be able to support palladium in different redox states. View Full-Text
Keywords: Heck reaction; catalysis; organometallic; palladium; frustrated Lewis pair; non-classical ligand Heck reaction; catalysis; organometallic; palladium; frustrated Lewis pair; non-classical ligand
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Tamang, S.R.; Hoefelmeyer, J.D. Chloro({2-[mesityl(quinolin-8-yl-κN)boryl]-3,5-dimethyl-phenyl}methyl-κC)palladium(II) as a Catalyst for Heck Reactions. Molecules 2015, 20, 12979-12991.

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