Organolanthanide constrained geometry complexes modified for catalysis: Synthesis, structure, and aminoalkene hydroamination properties of a pyrrolidine-substituted constrained geometry organolutetium complex

Afif M. Seyam; Bryan D. Stubbert; Tryg R. Jensen; James J. O'Donnell; Charlotte L. Stern; Tobin J. Marks

doi:10.1016/j.ica.2004.08.018

Organolanthanide constrained geometry complexes modified for catalysis: Synthesis, structure, and aminoalkene hydroamination properties of a pyrrolidine-substituted constrained geometry organolutetium complex

Afif M. Seyam, Bryan D. Stubbert, Tryg R. Jensen, James J. O'Donnell, Charlotte L. Stern, Tobin J. Marks

Northwestern University

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

45 Citations (Scopus)

Abstract

The reaction of the organolutetium complex (CGC′)LuCl ₃Li₂(THF), (1; CGC′ = [Me₂Si(3- pyrrolidinyl-1-η⁵-indenyl)(^tBuN)]^2-) with NaN(TMS)₂ provides a straightforward route to the halide-free organolutetium amido complex, (CGC′)LuN(TMS)₂(THF) (2). These new complexes were characterized by standard analytical methodology. The monomeric complex 2 crystallizes in the monoclinic space group P2₁/c with four molecules in a cell of dimensions a = 11.1566(6) Å, b = 14.9805(8) Å, c = 22.18007(12) Å, and β = 90.0620(10)°. Complex 2 is an active precatalyst for the intramolecular hydroamination/ cyclization of representative aminoalkenes with turnover frequencies as high as 205 h^-1 at room temperature.

Original language	English
Pages (from-to)	4029-4035
Number of pages	7
Journal	Inorganica Chimica Acta
Volume	357
Issue number	13
DOIs	https://doi.org/10.1016/j.ica.2004.08.018
Publication status	Published - Nov 1 2004

Keywords

Aminoalkene
Catalysis
Constrained geometry
Heterocycle
Hydroamination
Modified constrained geometry
Organolanthanide

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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Seyam, A. M., Stubbert, B. D., Jensen, T. R., O'Donnell, J. J., Stern, C. L., & Marks, T. J. (2004). Organolanthanide constrained geometry complexes modified for catalysis: Synthesis, structure, and aminoalkene hydroamination properties of a pyrrolidine-substituted constrained geometry organolutetium complex. Inorganica Chimica Acta, 357(13), 4029-4035. https://doi.org/10.1016/j.ica.2004.08.018

Organolanthanide constrained geometry complexes modified for catalysis : Synthesis, structure, and aminoalkene hydroamination properties of a pyrrolidine-substituted constrained geometry organolutetium complex. / Seyam, Afif M.; Stubbert, Bryan D.; Jensen, Tryg R.; O'Donnell, James J.; Stern, Charlotte L.; Marks, Tobin J.

In: Inorganica Chimica Acta, Vol. 357, No. 13, 01.11.2004, p. 4029-4035.

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

Seyam, AM, Stubbert, BD, Jensen, TR, O'Donnell, JJ, Stern, CL & Marks, TJ 2004, 'Organolanthanide constrained geometry complexes modified for catalysis: Synthesis, structure, and aminoalkene hydroamination properties of a pyrrolidine-substituted constrained geometry organolutetium complex', Inorganica Chimica Acta, vol. 357, no. 13, pp. 4029-4035. https://doi.org/10.1016/j.ica.2004.08.018

Seyam AM, Stubbert BD, Jensen TR, O'Donnell JJ, Stern CL, Marks TJ. Organolanthanide constrained geometry complexes modified for catalysis: Synthesis, structure, and aminoalkene hydroamination properties of a pyrrolidine-substituted constrained geometry organolutetium complex. Inorganica Chimica Acta. 2004 Nov 1;357(13):4029-4035. https://doi.org/10.1016/j.ica.2004.08.018

Seyam, Afif M. ; Stubbert, Bryan D. ; Jensen, Tryg R. ; O'Donnell, James J. ; Stern, Charlotte L. ; Marks, Tobin J. / Organolanthanide constrained geometry complexes modified for catalysis : Synthesis, structure, and aminoalkene hydroamination properties of a pyrrolidine-substituted constrained geometry organolutetium complex. In: Inorganica Chimica Acta. 2004 ; Vol. 357, No. 13. pp. 4029-4035.

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title = "Organolanthanide constrained geometry complexes modified for catalysis: Synthesis, structure, and aminoalkene hydroamination properties of a pyrrolidine-substituted constrained geometry organolutetium complex",

abstract = "The reaction of the organolutetium complex (CGC′)LuCl 3Li2(THF), (1; CGC′ = [Me2Si(3- pyrrolidinyl-1-η5-indenyl)(tBuN)]2-) with NaN(TMS)2 provides a straightforward route to the halide-free organolutetium amido complex, (CGC′)LuN(TMS)2(THF) (2). These new complexes were characterized by standard analytical methodology. The monomeric complex 2 crystallizes in the monoclinic space group P21/c with four molecules in a cell of dimensions a = 11.1566(6) {\AA}, b = 14.9805(8) {\AA}, c = 22.18007(12) {\AA}, and β = 90.0620(10)°. Complex 2 is an active precatalyst for the intramolecular hydroamination/ cyclization of representative aminoalkenes with turnover frequencies as high as 205 h-1 at room temperature.",

keywords = "Aminoalkene, Catalysis, Constrained geometry, Heterocycle, Hydroamination, Modified constrained geometry, Organolanthanide",

author = "Seyam, {Afif M.} and Stubbert, {Bryan D.} and Jensen, {Tryg R.} and O'Donnell, {James J.} and Stern, {Charlotte L.} and Marks, {Tobin J.}",

note = "Funding Information: Financial support from the National Science Foundation (CHE-0078998 and CHE-0415407) is gratefully acknowledged. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

year = "2004",

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doi = "10.1016/j.ica.2004.08.018",

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AU - Stubbert, Bryan D.

AU - Jensen, Tryg R.

AU - O'Donnell, James J.

AU - Stern, Charlotte L.

AU - Marks, Tobin J.

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N2 - The reaction of the organolutetium complex (CGC′)LuCl 3Li2(THF), (1; CGC′ = [Me2Si(3- pyrrolidinyl-1-η5-indenyl)(tBuN)]2-) with NaN(TMS)2 provides a straightforward route to the halide-free organolutetium amido complex, (CGC′)LuN(TMS)2(THF) (2). These new complexes were characterized by standard analytical methodology. The monomeric complex 2 crystallizes in the monoclinic space group P21/c with four molecules in a cell of dimensions a = 11.1566(6) Å, b = 14.9805(8) Å, c = 22.18007(12) Å, and β = 90.0620(10)°. Complex 2 is an active precatalyst for the intramolecular hydroamination/ cyclization of representative aminoalkenes with turnover frequencies as high as 205 h-1 at room temperature.

AB - The reaction of the organolutetium complex (CGC′)LuCl 3Li2(THF), (1; CGC′ = [Me2Si(3- pyrrolidinyl-1-η5-indenyl)(tBuN)]2-) with NaN(TMS)2 provides a straightforward route to the halide-free organolutetium amido complex, (CGC′)LuN(TMS)2(THF) (2). These new complexes were characterized by standard analytical methodology. The monomeric complex 2 crystallizes in the monoclinic space group P21/c with four molecules in a cell of dimensions a = 11.1566(6) Å, b = 14.9805(8) Å, c = 22.18007(12) Å, and β = 90.0620(10)°. Complex 2 is an active precatalyst for the intramolecular hydroamination/ cyclization of representative aminoalkenes with turnover frequencies as high as 205 h-1 at room temperature.

KW - Aminoalkene

KW - Catalysis

KW - Constrained geometry

KW - Heterocycle

KW - Hydroamination

KW - Modified constrained geometry

KW - Organolanthanide

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Organolanthanide constrained geometry complexes modified for catalysis: Synthesis, structure, and aminoalkene hydroamination properties of a pyrrolidine-substituted constrained geometry organolutetium complex

Abstract

Keywords

ASJC Scopus subject areas

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