Metal-assisted in situ formation of a tridentate acetylacetone ligand for complexation of fac-Re(CO)3+ for radiopharmaceutical applications

Paul D. Benny; Glenn A. Fugate; Adam O. Barden; Jennifer E. Morley; Elsa Silva-Lopez; Brendan Twamley

doi:10.1021/ic701996e

Metal-assisted in situ formation of a tridentate acetylacetone ligand for complexation of fac-Re(CO)₃⁺ for radiopharmaceutical applications

Paul D. Benny, Glenn A. Fugate, Adam O. Barden, Jennifer E. Morley, Elsa Silva-Lopez, Brendan Twamley

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

35 Scopus citations

Abstract

Reaction of [NEt₄]₂[ReBr₃(CO)₃] with 2,4-pentanedione (acac) yields a complex of the type fac-Re(acac)(OH ₂)(CO)₃ (1) under aqueous conditions. 1 was further reacted with a monodentate ligand (pyridine) to yield a fac-Re(acac)(pyridine) (CO)₃ complex (2). Complex 1 was found to react with primary amines to generate a Schiff base (imine) in aqueous solutions. When a mixed-nitrogen donor bidentate ligand, 2-(2-aminoethyl)pyridine, that has different coordination affinities for fac-Re(acac)(OH₂)(CO)₃ was utilized, a unique tridentate ligand was formed in situ utilizing a metal-assisted Schiff base formation to yield a complex fac-Re(CO) ₃(3[(2-phenylethyl)imino]-2-pentanone) (3). Tridentate ligand formation was found to occur only with the Re-coordinated acac ligand. Reactions of acac with fac-Re(CO)₃Br(2-(2-aminoethyl)pyridine) (4) or a mixture of [NEt₄]₂[ReBr₃(CO)₃], acac, and 2-(2-aminoethyl)pyridine did not yield the formation of complex 3 in water.

Original language	English
Pages (from-to)	2240-2242
Number of pages	3
Journal	Inorganic Chemistry
Volume	47
Issue number	7
DOIs	https://doi.org/10.1021/ic701996e
State	Published - Apr 7 2008
Externally published	Yes

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@article{d16b25fafce34f3892dfba8a699a2749,

title = "Metal-assisted in situ formation of a tridentate acetylacetone ligand for complexation of fac-Re(CO)3+ for radiopharmaceutical applications",

abstract = "Reaction of [NEt4]2[ReBr3(CO)3] with 2,4-pentanedione (acac) yields a complex of the type fac-Re(acac)(OH 2)(CO)3 (1) under aqueous conditions. 1 was further reacted with a monodentate ligand (pyridine) to yield a fac-Re(acac)(pyridine) (CO)3 complex (2). Complex 1 was found to react with primary amines to generate a Schiff base (imine) in aqueous solutions. When a mixed-nitrogen donor bidentate ligand, 2-(2-aminoethyl)pyridine, that has different coordination affinities for fac-Re(acac)(OH2)(CO)3 was utilized, a unique tridentate ligand was formed in situ utilizing a metal-assisted Schiff base formation to yield a complex fac-Re(CO) 3(3[(2-phenylethyl)imino]-2-pentanone) (3). Tridentate ligand formation was found to occur only with the Re-coordinated acac ligand. Reactions of acac with fac-Re(CO)3Br(2-(2-aminoethyl)pyridine) (4) or a mixture of [NEt4]2[ReBr3(CO)3], acac, and 2-(2-aminoethyl)pyridine did not yield the formation of complex 3 in water.",

author = "Benny, {Paul D.} and Fugate, {Glenn A.} and Barden, {Adam O.} and Morley, {Jennifer E.} and Elsa Silva-Lopez and Brendan Twamley",

year = "2008",

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doi = "10.1021/ic701996e",

language = "English",

volume = "47",

pages = "2240--2242",

journal = "Inorganic Chemistry",

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T1 - Metal-assisted in situ formation of a tridentate acetylacetone ligand for complexation of fac-Re(CO)3+ for radiopharmaceutical applications

AU - Benny, Paul D.

AU - Fugate, Glenn A.

AU - Barden, Adam O.

AU - Morley, Jennifer E.

AU - Silva-Lopez, Elsa

AU - Twamley, Brendan

PY - 2008/4/7

Y1 - 2008/4/7

N2 - Reaction of [NEt4]2[ReBr3(CO)3] with 2,4-pentanedione (acac) yields a complex of the type fac-Re(acac)(OH 2)(CO)3 (1) under aqueous conditions. 1 was further reacted with a monodentate ligand (pyridine) to yield a fac-Re(acac)(pyridine) (CO)3 complex (2). Complex 1 was found to react with primary amines to generate a Schiff base (imine) in aqueous solutions. When a mixed-nitrogen donor bidentate ligand, 2-(2-aminoethyl)pyridine, that has different coordination affinities for fac-Re(acac)(OH2)(CO)3 was utilized, a unique tridentate ligand was formed in situ utilizing a metal-assisted Schiff base formation to yield a complex fac-Re(CO) 3(3[(2-phenylethyl)imino]-2-pentanone) (3). Tridentate ligand formation was found to occur only with the Re-coordinated acac ligand. Reactions of acac with fac-Re(CO)3Br(2-(2-aminoethyl)pyridine) (4) or a mixture of [NEt4]2[ReBr3(CO)3], acac, and 2-(2-aminoethyl)pyridine did not yield the formation of complex 3 in water.

AB - Reaction of [NEt4]2[ReBr3(CO)3] with 2,4-pentanedione (acac) yields a complex of the type fac-Re(acac)(OH 2)(CO)3 (1) under aqueous conditions. 1 was further reacted with a monodentate ligand (pyridine) to yield a fac-Re(acac)(pyridine) (CO)3 complex (2). Complex 1 was found to react with primary amines to generate a Schiff base (imine) in aqueous solutions. When a mixed-nitrogen donor bidentate ligand, 2-(2-aminoethyl)pyridine, that has different coordination affinities for fac-Re(acac)(OH2)(CO)3 was utilized, a unique tridentate ligand was formed in situ utilizing a metal-assisted Schiff base formation to yield a complex fac-Re(CO) 3(3[(2-phenylethyl)imino]-2-pentanone) (3). Tridentate ligand formation was found to occur only with the Re-coordinated acac ligand. Reactions of acac with fac-Re(CO)3Br(2-(2-aminoethyl)pyridine) (4) or a mixture of [NEt4]2[ReBr3(CO)3], acac, and 2-(2-aminoethyl)pyridine did not yield the formation of complex 3 in water.

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Metal-assisted in situ formation of a tridentate acetylacetone ligand for complexation of fac-Re(CO)₃⁺ for radiopharmaceutical applications

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