Issue 13, 2013

Electronic control in frustrated Lewis pair chemistry: adduct formation of intramolecular FLP systems with –P(C6F5)2 Lewis base components

Abstract

2-Propenylbis(pentafluorophenyl)phosphane adds Piers’ borane [HB(C6F5)2] with anti-Markovnikov orientation to yield the intramolecular vicinal frustrated P/B Lewis pair 10. The FLP 10 adds pyridine, acetonitrile or alkyl isocyanides to form simple boron Lewis acid adducts 11–14, all of which were characterized by X-ray diffraction. The FLP 10 reacts with trans-cinnamic aldehyde to give a boron carbonyl adduct 15 that was characterized by an X-ray crystal structure analysis. In contrast, the geminal FLP (C6F5)2P–CHEt–B(C6F5)2 (3) undergoes 1,2-carbonyl addition reactions with benzaldehyde or trans-cinnamic aldehyde to yield the respective five-membered heterocyclic products (7, 8, both characterized by X-ray diffraction). The FLP 10 undergoes 1,2-P/B addition to p-tolylacetylene and to 2-methylbutenyne, respectively, to yield the corresponding six-membered heterocyclic products 17 and 18, respectively (both were characterized by X-ray diffraction).

Graphical abstract: Electronic control in frustrated Lewis pair chemistry: adduct formation of intramolecular FLP systems with –P(C6F5)2 Lewis base components

Supplementary files

Article information

Article type
Paper
Submitted
23 Nov 2012
Accepted
13 Dec 2012
First published
17 Dec 2012

Dalton Trans., 2013,42, 4487-4499

Electronic control in frustrated Lewis pair chemistry: adduct formation of intramolecular FLP systems with –P(C6F5)2 Lewis base components

A. Stute, G. Kehr, C. G. Daniliuc, R. Fröhlich and G. Erker, Dalton Trans., 2013, 42, 4487 DOI: 10.1039/C2DT32806B

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