Aerobic Oxidative Coupling of 2-Aminonaphthalenes by Homogenous Nonheme Iron Catalysts

Vlada Vershinin; Li Noy Feruz; Hagit Forkosh; Lina Kertzman; Anna Libman; Jordi Burés; Doron Pappo

doi:https://doi.org/10.1021/acscatal.4c01839

Aerobic Oxidative Coupling of 2-Aminonaphthalenes by Homogenous Nonheme Iron Catalysts

Vlada Vershinin, Li Noy Feruz, Hagit Forkosh, Lina Kertzman, Anna Libman, Jordi Burés, Doron Pappo

Department of Chemistry

Ben-Gurion University of the Negev

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

Abstract

An efficient and general aerobic oxidative coupling method to prepare 1,1′-binaphthyl-2,2′-diamines (BINAMs) from N-substituted-2-aminonaphthalene (1) based on [Fe^III(cyclen)(Cl)₂]Cl catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) at room temperature is reported. The highly selective conditions were applied to prepare a list of N,N′-dialkyl-, N,N′-dibenzyl-, and N,N′-diaryl-BINAMs with moderate to high yields. Based on mechanistic studies, which include control experiments and variable time normalization analysis, it is suggested that the coupling between [Fe^III(cyclen)(1)(OOH)]⁺² and 2-aminonaphthalene 1 is the key irreversible step in the catalytic cycle.

Original language	American English
Pages (from-to)	8261-8269
Number of pages	9
Journal	ACS Catalysis
Volume	14
Issue number	11
DOIs	https://doi.org/10.1021/acscatal.4c01839
State	Published - 7 Jun 2024

Keywords

1,1′-binaphthyl-2,2′-diamine (BINAM)
2-aminonaphthalene
aerobic oxidative coupling
nonheme iron catalysis
variable time normalization analysis

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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https://doi.org/10.1021/acscatal.4c01839

Cite this

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title = "Aerobic Oxidative Coupling of 2-Aminonaphthalenes by Homogenous Nonheme Iron Catalysts",

abstract = "An efficient and general aerobic oxidative coupling method to prepare 1,1′-binaphthyl-2,2′-diamines (BINAMs) from N-substituted-2-aminonaphthalene (1) based on [FeIII(cyclen)(Cl)2]Cl catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) at room temperature is reported. The highly selective conditions were applied to prepare a list of N,N′-dialkyl-, N,N′-dibenzyl-, and N,N′-diaryl-BINAMs with moderate to high yields. Based on mechanistic studies, which include control experiments and variable time normalization analysis, it is suggested that the coupling between [FeIII(cyclen)(1)(OOH)]+2 and 2-aminonaphthalene 1 is the key irreversible step in the catalytic cycle.",

keywords = "1,1′-binaphthyl-2,2′-diamine (BINAM), 2-aminonaphthalene, aerobic oxidative coupling, nonheme iron catalysis, variable time normalization analysis",

author = "Vlada Vershinin and Feruz, {Li Noy} and Hagit Forkosh and Lina Kertzman and Anna Libman and Jordi Bur{\'e}s and Doron Pappo",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

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AU - Vershinin, Vlada

AU - Feruz, Li Noy

AU - Forkosh, Hagit

AU - Kertzman, Lina

AU - Libman, Anna

AU - Burés, Jordi

AU - Pappo, Doron

PY - 2024/6/7

Y1 - 2024/6/7

N2 - An efficient and general aerobic oxidative coupling method to prepare 1,1′-binaphthyl-2,2′-diamines (BINAMs) from N-substituted-2-aminonaphthalene (1) based on [FeIII(cyclen)(Cl)2]Cl catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) at room temperature is reported. The highly selective conditions were applied to prepare a list of N,N′-dialkyl-, N,N′-dibenzyl-, and N,N′-diaryl-BINAMs with moderate to high yields. Based on mechanistic studies, which include control experiments and variable time normalization analysis, it is suggested that the coupling between [FeIII(cyclen)(1)(OOH)]+2 and 2-aminonaphthalene 1 is the key irreversible step in the catalytic cycle.

AB - An efficient and general aerobic oxidative coupling method to prepare 1,1′-binaphthyl-2,2′-diamines (BINAMs) from N-substituted-2-aminonaphthalene (1) based on [FeIII(cyclen)(Cl)2]Cl catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) at room temperature is reported. The highly selective conditions were applied to prepare a list of N,N′-dialkyl-, N,N′-dibenzyl-, and N,N′-diaryl-BINAMs with moderate to high yields. Based on mechanistic studies, which include control experiments and variable time normalization analysis, it is suggested that the coupling between [FeIII(cyclen)(1)(OOH)]+2 and 2-aminonaphthalene 1 is the key irreversible step in the catalytic cycle.

KW - 1,1′-binaphthyl-2,2′-diamine (BINAM)

KW - 2-aminonaphthalene

KW - aerobic oxidative coupling

KW - nonheme iron catalysis

KW - variable time normalization analysis

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DO - https://doi.org/10.1021/acscatal.4c01839

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JO - ACS Catalysis

JF - ACS Catalysis

IS - 11

ER -

Aerobic Oxidative Coupling of 2-Aminonaphthalenes by Homogenous Nonheme Iron Catalysts

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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