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Issue 20, 2015
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Direct synthesis of a geminal zwitterionic phosphonium/hydridoborate system – developing an alternative tool for generating frustrated Lewis pair hydrogen activation systems

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Abstract

A convenient way to a new class of geminal Mes2PH+/B(C6F5)2H pairs is presented. It utilizes triflic acid addition to trans-Mes2PCH[double bond, length as m-dash]CHB(C6F5)2 followed by triflate/hydride exchange. Thermally induced ring-closure gave a phosphonium/boratacyclopropane zwitterion 8 which formed the Mes2PH(CHMe)B(C6F5)2H P/B FLP-H2 product 10 by subsequent treatment with triflic acid and a silane, or alternatively with dihydrogen at 90 °C. The product 10 is an active catalyst for the hydrogenation of a variety of unsaturated organic substrates, including a quinoline derivative. Treatment of compound 8 with HB(C6F5)2 gave a bifunctional borane 14 which selectively reduced carbon monoxide to the formyl stage.

Graphical abstract: Direct synthesis of a geminal zwitterionic phosphonium/hydridoborate system – developing an alternative tool for generating frustrated Lewis pair hydrogen activation systems

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Supplementary files

Article information


Submitted
31 Mar 2015
Accepted
15 Apr 2015
First published
15 Apr 2015

Org. Biomol. Chem., 2015,13, 5783-5792
Article type
Paper

Direct synthesis of a geminal zwitterionic phosphonium/hydridoborate system – developing an alternative tool for generating frustrated Lewis pair hydrogen activation systems

J. Yu, G. Kehr, C. G. Daniliuc, C. Bannwarth, S. Grimme and G. Erker, Org. Biomol. Chem., 2015, 13, 5783
DOI: 10.1039/C5OB00634A

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