Synthesis of the First Stable Palladium Allenylidene Complexes

Kessler, Florian; Szesni, Normen; Põhako, Kaija; Weibert, Bernhard; Fischer, Helmut

Synthesis of the First Stable Palladium Allenylidene Complexes

Files

om800843e.pdf(679.62 KB)

Date

2009

Authors

Kessler, Florian

Szesni, Normen

Põhako, Kaija

Weibert, Bernhard

Fischer, Helmut

Publication type

Journal article

Published in

Organometallics ; 28 (2009), 1. - pp. 348-354. - ISSN 0276-7333. - eISSN 1520-6041

Abstract

Oxidative addition of BrCCC(=O)NR2 to [Pd(PPh3)4] affords the trans-alkynylbromopalladium complexes trans-[Br(PPh3)2Pd−CCC(=O)NR2] (NR2 = NMe2 (2a), N(CH2)4) (2b)). Subsequent reaction of 2a,b with PiPr3 in excess gives trans-[Br(PiPr3)2Pd−CCC(=O)NR2] (5a,b). The analogous reaction of 2b with P(C6H4OMe-4)3 gives trans-[Br(P{C6H4OMe-4}3)2Pd−CCC(=O)NR2] (7b), and that of 2a with trifluoroacetate gives trans-[(F3CCOO)(PPh3)2Pd−CCC(=O)NMe2] (9a). Methylation of 2a,b, 7b, and 9a with either MeOTf or [Me3O]BF4 and ethylation of 2a,b with [Et3O]BF4 yield the first cationic allenylidene complexes of palladium, trans-[R*(PR′3)2Pd−CCC(OMe)NR2]+X− (R* = Br, CF3COO; R′ = Ph, C6H4OMe-4, iPr; X = OTf, BF4).

Subject (DDC)

540 Chemistry

Keywords

Allenylidene complexes,Palladium,Alkinyl complexes

Cite This

ISO 690

KESSLER, Florian, Normen SZESNI, Kaija PÕHAKO, Bernhard WEIBERT, Helmut FISCHER, 2009. Synthesis of the First Stable Palladium Allenylidene Complexes. In: Organometallics. 28(1), pp. 348-354. ISSN 0276-7333. eISSN 1520-6041. Available under: doi: 10.1021/om800843e

BibTex

@article{Kessler2009Synth-9993,
  year={2009},
  doi={10.1021/om800843e},
  title={Synthesis of the First Stable Palladium Allenylidene Complexes},
  number={1},
  volume={28},
  issn={0276-7333},
  journal={Organometallics},
  pages={348--354},
  author={Kessler, Florian and Szesni, Normen and Põhako, Kaija and Weibert, Bernhard and Fischer, Helmut}
}

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    <dcterms:abstract xml:lang="eng">Oxidative addition of BrCCC(=O)NR2 to [Pd(PPh3)4] affords the trans-alkynylbromopalladium complexes trans-[Br(PPh3)2Pd−CCC(=O)NR2] (NR2 = NMe2 (2a), N(CH2)4) (2b)). Subsequent reaction of 2a,b with PiPr3 in excess gives trans-[Br(PiPr3)2Pd−CCC(=O)NR2] (5a,b). The analogous reaction of 2b with P(C6H4OMe-4)3 gives trans-[Br(P{C6H4OMe-4}3)2Pd−CCC(=O)NR2] (7b), and that of 2a with trifluoroacetate gives trans-[(F3CCOO)(PPh3)2Pd−CCC(=O)NMe2] (9a). Methylation of 2a,b, 7b, and 9a with either MeOTf or [Me3O]BF4 and ethylation of 2a,b with [Et3O]BF4 yield the first cationic allenylidene complexes of palladium, trans-[R*(PR′3)2Pd−CCC(OMe)NR2]+X− (R* = Br, CF3COO; R′ = Ph, C6H4OMe-4, iPr; X = OTf, BF4).</dcterms:abstract>
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