A PCN ligand system. Exclusive C-C activation with rhodium(I) and C-H activation with platinum(II)

Mark Gandelman; Arkadi Vigalok; Linda J.W. Shimon; David Milstein

doi:10.1021/om9703200

A PCN ligand system. Exclusive C-C activation with rhodium(I) and C-H activation with platinum(II)

Mark Gandelman, Arkadi Vigalok, Linda J.W. Shimon, David Milstein

Weizmann Institute of Science

Research output: Contribution to journal › Article › peer-review

119 Scopus citations

Abstract

Reaction of the new aromatic aminophosphine ligand 1-((diethylamino)methyl)-3-((di-tertbutylphosphino)methyl)-2,4,6- trimethylbenzene (4) with [Rh(COE)₂Cl]₂ (COE = cyclooctene) or with [Rh(ethylene)₂Cl]₂ at room temperature results in selective carbon-carbon bond activation, yielding the complex ClRh(CH₃)[C₆H(CH₃)₂(CH ₂N(C₂H₅)₂)(CH ₂P(t-Bu)₂)] (5). No competing C-H activation was observed during the course of the reaction. When 4 was reacted with (COD)PtCl₂ (COD = cyclooctadiene), selective C-H activation of the methyl group situated between the phosphine and amine groups took place, with concomitant intramolecular H transfer to the amine ligand, resulting in the zwitterionic Pt(II) complex Cl₂PtCH₂(C₆H(CH₃) ₂(CH₂NH(C₂H₅)₂(CH ₂P(t-Bu)₂) (11).

Original language	English
Pages (from-to)	3981-3986
Number of pages	6
Journal	Organometallics
Volume	16
Issue number	18
DOIs	https://doi.org/10.1021/om9703200
State	Published - 2 Sep 1997
Externally published	Yes

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@article{68a4503450164db8971168746b0ba117,

title = "A PCN ligand system. Exclusive C-C activation with rhodium(I) and C-H activation with platinum(II)",

abstract = "Reaction of the new aromatic aminophosphine ligand 1-((diethylamino)methyl)-3-((di-tertbutylphosphino)methyl)-2,4,6- trimethylbenzene (4) with [Rh(COE)2Cl]2 (COE = cyclooctene) or with [Rh(ethylene)2Cl]2 at room temperature results in selective carbon-carbon bond activation, yielding the complex ClRh(CH3)[C6H(CH3)2(CH 2N(C2H5)2)(CH 2P(t-Bu)2)] (5). No competing C-H activation was observed during the course of the reaction. When 4 was reacted with (COD)PtCl2 (COD = cyclooctadiene), selective C-H activation of the methyl group situated between the phosphine and amine groups took place, with concomitant intramolecular H transfer to the amine ligand, resulting in the zwitterionic Pt(II) complex Cl2PtCH2(C6H(CH3) 2(CH2NH(C2H5)2(CH 2P(t-Bu)2) (11).",

author = "Mark Gandelman and Arkadi Vigalok and Shimon, {Linda J.W.} and David Milstein",

year = "1997",

month = sep,

day = "2",

doi = "10.1021/om9703200",

language = "אנגלית",

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journal = "Organometallics",

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publisher = "American Chemical Society",

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T1 - A PCN ligand system. Exclusive C-C activation with rhodium(I) and C-H activation with platinum(II)

AU - Gandelman, Mark

AU - Vigalok, Arkadi

AU - Shimon, Linda J.W.

AU - Milstein, David

PY - 1997/9/2

Y1 - 1997/9/2

N2 - Reaction of the new aromatic aminophosphine ligand 1-((diethylamino)methyl)-3-((di-tertbutylphosphino)methyl)-2,4,6- trimethylbenzene (4) with [Rh(COE)2Cl]2 (COE = cyclooctene) or with [Rh(ethylene)2Cl]2 at room temperature results in selective carbon-carbon bond activation, yielding the complex ClRh(CH3)[C6H(CH3)2(CH 2N(C2H5)2)(CH 2P(t-Bu)2)] (5). No competing C-H activation was observed during the course of the reaction. When 4 was reacted with (COD)PtCl2 (COD = cyclooctadiene), selective C-H activation of the methyl group situated between the phosphine and amine groups took place, with concomitant intramolecular H transfer to the amine ligand, resulting in the zwitterionic Pt(II) complex Cl2PtCH2(C6H(CH3) 2(CH2NH(C2H5)2(CH 2P(t-Bu)2) (11).

AB - Reaction of the new aromatic aminophosphine ligand 1-((diethylamino)methyl)-3-((di-tertbutylphosphino)methyl)-2,4,6- trimethylbenzene (4) with [Rh(COE)2Cl]2 (COE = cyclooctene) or with [Rh(ethylene)2Cl]2 at room temperature results in selective carbon-carbon bond activation, yielding the complex ClRh(CH3)[C6H(CH3)2(CH 2N(C2H5)2)(CH 2P(t-Bu)2)] (5). No competing C-H activation was observed during the course of the reaction. When 4 was reacted with (COD)PtCl2 (COD = cyclooctadiene), selective C-H activation of the methyl group situated between the phosphine and amine groups took place, with concomitant intramolecular H transfer to the amine ligand, resulting in the zwitterionic Pt(II) complex Cl2PtCH2(C6H(CH3) 2(CH2NH(C2H5)2(CH 2P(t-Bu)2) (11).

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SN - 0276-7333

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JO - Organometallics

JF - Organometallics

IS - 18

ER -

A PCN ligand system. Exclusive C-C activation with rhodium(I) and C-H activation with platinum(II)

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