Single and double deprotonation/dearomatization of the N,S-donor pyridinophane ligand in ruthenium complexes

Dinh, Minh Hoan; Gridneva, Tatiana; Karimata, Ayumu; Garcia-Roca, Alèria; Pruchyathamkorn, Jiratheep; Patil, Pradnya H.; Petrov, Andrey V.; Sarbajna, Abir; Lapointe, Sébastien; Khaskin, Eugene; Fayzullin, Robert R.; Khusnutdinova, Julia R.

doi:10.1039/d2dt02219b

Dalton Trans.

2022

DOI: 10.1039/d2dt02219b

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Single and double deprotonation/dearomatization of the N,S-donor pyridinophane ligand in ruthenium complexes

Minh Hoan Dinh

Tatiana Gridneva

Ayumu Karimata

et al.

Abstract: We report a series of ruthenium complexes with a tetradentate N,S-donor ligand, 2,11-dithia[3.3](2,6)pyridinophane (N2S2) that undergo single and double deprotonation in the presence of a base leading to the deprotonation...

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Cited by 3 publications

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Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

Sheokand

Balakrishna

2023

Inorg. Chem.

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We describe the synthesis of a triazolyl-pyridine-based aminophosphine, N-(diphenylphosphaneyl)-6-(1-phenyl)-1H- (1,2,3-triazol-4-yl)H)N hereafter], and its palladium and platinum complexes and their catalytic application. The reaction of 1 with [M(COD)Cl 2 ] (M = Pd or Pt) afforded the cationic complex [(MCl){PN(H)N}-κ 3 -P,N,N]Cl [M = Pd (2) or Pt (3)]. Alternatively, compounds 2 and 3 were also synthesized by treating [2,6-{H 2 N(C 5 H 3 N)(C 2 HN 3 C 6 H 5 )}] (A) with [M(COD)Cl 2 ] (M = Pd or Pt), followed by the addition of stoichiometric amounts of PPh 2 Cl and Et 3 N. The neutral, dearomatized complexes [(MCl){PNN}-κ 3 -P,N,N] [M = Pd (4) or Pt (5)] were prepared by the deprotonation of the NH of 2 and 3 with 1 equiv of t BuOK. Compounds 4 and 5 were also synthesized stepwise by treating [2,6-{H 2 N(C 5 H 3 N)(C 2 HN 3 C 6 H 5 )}] (A) with [M-(COD)Cl 2 ] (M = Pd or Pt) to give intermediate complexes [{MCl 2 }2,6-{NH 2 (C 5 H 3 N)(C 2 HN 3 C 6 H 5 )-κ 2 -N,N}] [M = Pd (B) or Pt (C)], which were subsequently phosphinated. The in situ-generated PNN ligand-stabilized Pd nanoparticles from compound 2 catalyzed the annulation of o-bromobenzaldehyde with alkynes to yield indenone derivatives. Mechanistic investigations suggested that the reaction was catalyzed by Pd nanoparticles (Pd@2) generated from compound 2 and proceeded through sequential oxidative addition, alkyne insertion, and reductive elimination steps to produce indanone products.

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Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

Sheokand

Balakrishna

2023

Inorg. Chem.

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Unveiling the Potential of SNS-Ni Complex for Establishing C–N Bonds: An Approach toward Chemoselectivity

Sharma,

Mondal,

Maji

et al. 2024

Organometallics

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Recent research has focused a lot on using the borrowing hydrogen (BH) approach to react amines with alcohols to convert a C−O bond into a C−N bond. However, the notion of chemoselectivity in BH-mediated N-alkylation of amines has rarely been studied. Herein, we have demonstrated the application of a synthesized SNS-Ni complex constructing various C−N bonds via the coupling of diverse amines with various alcohols. Delightfully, the catalytic protocol also activates challenging C4−C16 aliphatic alcohols. Aryl amino alcohols are selectively N-alkylated with different alcohols, while keeping the OH group intact in the amino alcohol portion. Furthermore, without reducing the distal unsaturation, the catalytic technique was also successfully employed for the chemoselective N-alkylation of different fatty alcohols. The preliminary mechanistic investigation suggests alkylation occurs via a nonradical borrowing hydrogen pathway.

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A strategic approach for Csp³–H functionalization of 9H-fluorene: an acceptorless dehydrogenation and borrowing hydrogen approach

Sharma

Mondal

Samanta

et al. 2023

Catal. Sci. Technol.

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Single and double deprotonation/dearomatization of the N,S-donor pyridinophane ligand in ruthenium complexes

Abstract: We report a series of ruthenium complexes with a tetradentate N,S-donor ligand, 2,11-dithia[3.3](2,6)pyridinophane (N2S2) that undergo single and double deprotonation in the presence of a base leading to the deprotonation...

Cited by 3 publications

References 62 publications

Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

Unveiling the Potential of SNS-Ni Complex for Establishing C–N Bonds: An Approach toward Chemoselectivity

A strategic approach for Csp³–H functionalization of 9H-fluorene: an acceptorless dehydrogenation and borrowing hydrogen approach

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Single and double deprotonation/dearomatization of the N,S-donor pyridinophane ligand in ruthenium complexes

Abstract: We report a series of ruthenium complexes with a tetradentate N,S-donor ligand, 2,11-dithia[3.3](2,6)pyridinophane (N2S2) that undergo single and double deprotonation in the presence of a base leading to the deprotonation...

Cited by 3 publications

References 62 publications

Cationic and Neutral PdII and PtII Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

Cationic and Neutral PdII and PtII Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

Unveiling the Potential of SNS-Ni Complex for Establishing C–N Bonds: An Approach toward Chemoselectivity

A strategic approach for Csp3–H functionalization of 9H-fluorene: an acceptorless dehydrogenation and borrowing hydrogen approach

Contact Info

Product

Resources

About

Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

A strategic approach for Csp³–H functionalization of 9H-fluorene: an acceptorless dehydrogenation and borrowing hydrogen approach