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Naphthalene Exchange in [Re(η6-napht)2]+ with Pharmaceuticals Leads to Highly Functionalized Sandwich Complexes [M(η6-pharm)2]+ (M=Re/99mTc)


Nadeem, Qaisar; Battistin, Federica; Blacque, Olivier; Alberto, Roger (2022). Naphthalene Exchange in [Re(η6-napht)2]+ with Pharmaceuticals Leads to Highly Functionalized Sandwich Complexes [M(η6-pharm)2]+ (M=Re/99mTc). Chemistry - A European Journal, 28(5):e202103566.

Abstract

Bis-arene sandwich complexes are generally prepared by the Fischer-Hafner reaction, which conditions are incompatible with most O- and N- functional groups. We report a new way for the synthesis of sandwich type complexes [Re(η6-arene)2]+ and [Re(η6-arene)(η6-benzene)]+ from [Re(η6-napht)2]+ and [Re(η6-napht)(η6-benzene)]+, with functionalized arenes and pharmaceuticals. N-methylpyrrolidine (NMP) facilitates the substitution of naphthalene with the incoming arene. A series of fully characterized rhenium sandwich complexes with simple arenes, such as aniline, as well as with active compounds like lidocaine and melatonin are presented. With these rhenium compounds in hand, the radioactive sandwich complexes [99mTc(η6-pharm)2]+ (pharm=pharmaceutical) can be unambiguously confirmed. The direct labelling of pharmaceuticals with 99mTc through η6-coordination to phenyl rings and the confirmation of the structures with the rhenium homologues opens a path into molecular theranostics.

Abstract

Bis-arene sandwich complexes are generally prepared by the Fischer-Hafner reaction, which conditions are incompatible with most O- and N- functional groups. We report a new way for the synthesis of sandwich type complexes [Re(η6-arene)2]+ and [Re(η6-arene)(η6-benzene)]+ from [Re(η6-napht)2]+ and [Re(η6-napht)(η6-benzene)]+, with functionalized arenes and pharmaceuticals. N-methylpyrrolidine (NMP) facilitates the substitution of naphthalene with the incoming arene. A series of fully characterized rhenium sandwich complexes with simple arenes, such as aniline, as well as with active compounds like lidocaine and melatonin are presented. With these rhenium compounds in hand, the radioactive sandwich complexes [99mTc(η6-pharm)2]+ (pharm=pharmaceutical) can be unambiguously confirmed. The direct labelling of pharmaceuticals with 99mTc through η6-coordination to phenyl rings and the confirmation of the structures with the rhenium homologues opens a path into molecular theranostics.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:General Chemistry, Catalysis, Organic Chemistry
Language:English
Date:24 January 2022
Deposited On:13 Jan 2022 14:37
Last Modified:27 Mar 2024 03:05
Publisher:Wiley-VCH Verlag
ISSN:0947-6539
OA Status:Hybrid
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/chem.202103566
  • Content: Published Version
  • Language: English
  • Licence: Creative Commons: Attribution 4.0 International (CC BY 4.0)