Functional group chemistry at intramolecular frustrated Lewis pairs: substituent exchange at the Lewis acid site with 9-BBN

Markus Erdmann; Christian Rösener; Thorsten Holtrichter-Rößmann; Constantin G. Daniliuc; Roland Fröhlich; Werner Uhl; Ernst-Ulrich Würthwein; Gerald Kehr; Gerhard Erker

doi:10.1039/C2DT31737K

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Dalton Transactions

Issue 3, 2013

The international journal for inorganic, organometallic and bioinorganic chemistry

Impact Factor 3.838 48 Issues per Year Indexed in MEDLINE

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Paper

Functional group chemistry at intramolecular frustrated Lewis pairs: substituent exchange at the Lewis acid site with 9-BBN

Markus Erdmann,^a Christian Rösener,^b Thorsten Holtrichter-Rößmann,^a Constantin G. Daniliuc,^a Roland Fröhlich,^a Werner Uhl,*^b Ernst-Ulrich Würthwein,*^a Gerald Kehr^a and Gerhard Erker*^a

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Organisch-Chemisches Institut, Universität Münster, Corrensstraße 40, 48149 Münster, Germany
E-mail: erker@uni-muenster.de ;
Fax: +49 251 83-36503+49 251 83-39772

Institut für Anorganische und Analytische Chemie, Corrensstrasse 30, 48149 Münster, Germany
E-mail: uhlw@uni-muensdter.de ;
Fax: +49 251 83-36660 ;
Tel: +49 251 83-36610

Dalton Trans., 2013,42, 709-718

DOI: 10.1039/C2DT31737K
Received 31 Jul 2012, Accepted 06 Sep 2012
First published online 07 Sep 2012

This article is part of themed collection: Boranes and borohydrides

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Abstract
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The vicinal frustrated P/B Lewis pair (FLP) Mes₂PCH₂CH₂B(C₆F₅)₂ reacts with 9-borabicyclo[3.3.1]nonane (9-BBN) by C₆F₅vs. H exchange at boron to give the new [B]–H functionalized FLP Mes₂PCH₂CH₂B(H)(C₆F₅) (4) and 9-C₆F₅–BBN. The latter was characterized as an isonitrile adduct by X-ray diffraction. The new FLP 4 forms an adduct with pyridine and it undergoes clean hydroboration reactions with 1-pentyne or added styrene or dimesitylvinylphosphane. The products formed stable adducts with pyridine; two such examples were also characterized by X-ray crystal structure analysis. A similar alkyl vs. hydrogen exchange was observed upon treatment of an Al/N based Lewis pair, iBu₂Al–(Me₃Si)C [double bond, length as m-dash] C(H)–N(CH₂CH₂)₂NMe (14), with 9-BBN.