Aerobic oxidative coupling of alcohols and amines towards imine formation by a dicopper(I,I) catalyst

Dutta, Indranil; De, Subhabrata; Yadav, Sudhir; Mondol, Ranajit; Bera, Jitendra K.

doi:10.1016/j.jorganchem.2017.05.009

Cited by 23 publications

(20 citation statements)

References 98 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…They are (1) the direct coupling of alcohols and amines under aerobic or anaerobic condition and the by‐products are water and hydrogen, (2) oxidation of primary amines to imines through NH‐imine intermediate and (3) the oxidative dehydrogenation of secondary amines . The direct coupling of alcohols and amines was catalyzed by various noble (Ru,, Pd,, Au, and Rh) as well as non‐noble metals (Co, Fe and Cu) under air or inert atmosphere, and heterogeneous catalysts were also reported. The catalysts promote direct dehydrogenation of alcohols followed by coupling.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

et al. 2019

View full text Add to dashboard Cite

Three copper(I) complexes, [CuCl(L)(PPh 3 ) 2 ] [L = FL (1), BL (2) or TL (3)] were prepared from [(PPh 3 ) 2 Cu-(μ-Cl) 2 Cu(PPh 3 )] and N-carbamothioylfuran-2-carboxamide (FL), N-carbamothioylbenzamide (BL) or N-carbamothioylthiophene-2-carboxamide (TL) ligands in benzene and four-coordinated tetrahedral copper complexes were well characterized by various spectroscopic techniques (UV/Vis, FT-IR, 1 H NMR, 13 C NMR and 31 P NMR). The molecular structure of the ligands (FL and BL) and complexes was established from single-crystal X-ray diffraction studies. Copper complexes have been shown to cata- [a]

show abstract

Section: Introductionmentioning

confidence: 99%

Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

et al. 2019

View full text Add to dashboard Cite

show abstract

“…As reported by Bera et al., two dicopper(I) complexes supported by either 1,8‐naphthyridine‐based ligands with two mesitylimine (MI) groups [Cu 2 (μ‐Cl) 2 (μ‐κ 2 :κ 2 ‐NAPY‐MI)] ( 16 ) or two camphor‐pyrazole (CP) substituents [Cu 2 (μ‐Cl) 2 (μ‐κ 2 :κ 2 ‐NAPY‐CP)] ( 17 ) were synthesized for testing their catalytic activity in organic transformations (see below) . Both 16 and 17 were essentially isostrctural with two Cu atoms being bridged by one tetradentate 1,8‐naphthyridine, and both featured a butterfly‐shaped Cu 2 (μ‐Cl) 2 unit.…”

Section: Intramolecular Cuprophilic Interactions In Cui Complexesmentioning

confidence: 99%

“…2019, 25,8936 -8954 www.chemeurj.org CP)] (17)w ere synthesized for testing their catalytic activity in organic transformations( see below). [157,158] Both 16 and 17 were essentially isostrctural with two Cu atoms being bridged by one tetradentate1 ,8-naphthyridine, and both featured a butterfly-shaped Cu 2 (m-Cl) 2 unit. The Cu-Cu distances in 16 and 17 were 2.558(2) and 2.6432(11) ,r espectively,l onger than those of 1-15,e xcluding 11,p resumably due to each copperc enter with ah igherc oordinationn umber of four.…”

Section: Nitrogen Donor-supported Dicopper(i) Complexesmentioning

confidence: 99%

Cuprophilic Interactions in and between Molecular Entities

Harisomayajula

Makovetskyi

Tsai

2019

Chemistry A European J

145

127

View full text Add to dashboard Cite

Despite being weak attractive forces, closed‐shell metallophilic interactions play important roles in the Group 11 metal complexes on their diverse structural and physical features. A plethora of experimental and computational studies has thus been dedicated to such weak attractive d10–d10 interactions, particularly aurophilic and argentophilic interactions. Although d10–d10 CuI–CuI forces had been recognized for four decades, cuprophilic interactions are less explored and they are best evidenced by single‐crystal X‐ray crystallographic analysis on CuI complexes and aggregates thereof, by which precise information about the Cu⋅⋅⋅Cu contacts, shorter than the sum of two van der Waals radii (3.92 Å) between the copper centers concerned can be obtained. Based on recently compelling experimental and spectroscopic evidence for intra‐ and intermolecular cuprophilic interactions in copper chemistry, the present Minireview summarizes recent progress in the past three decades in the synthesis and structures of multinuclear homometallic copper complexes, whereby supported and unsupported d10–d10 CuI–CuI interactions are at work.

show abstract

“…Several homogeneous and heterogeneous transition metal catalysts for the synthesis of imines, such as Ru, Ir, Fe, Mn, Os, Co, Cu, Au/TiO 2 , Pd/DNA, Pd/ZrO 2, MOF were reported. Ruthenium complexes, well known for their effective catalytic activity in huge assortment of organic transformation reactions, are among the most useful catalysts for acceptorless dehydrogenative coupling of imines (see Figure ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Imines via Reactions of Benzyl Alcohol with Amines Using Half‐Sandwich (η⁶‐p‐cymene) Ruthenium(II) Complexes Stabilised by 2‐aminofluorene Derivatives

Vinoth

Indira

Bharathi

et al. 2019

Applied Organom Chemis

View full text Add to dashboard Cite

A new class of half-sandwich (η 6 -p-cymene) ruthenium(II) complexes supported by 2-aminofluorene derivatives [Ru(η 6 -p-cymene)(Cl)(L)] (L = 2-(((9H-fluoren-2-yl)imino)methyl)phenol (L 1 ), 2-(((9H-fluoren-2-yl)imino) methyl)-3-methoxyphenol (L 2 ), 1-(((9H-fluoren-2-yl)imino)methyl)naphthalene-2-ol (L 3 ) and N-((1H-pyrrol-2-yl)methylene)-9H-fluorene-2-amine (L 4 )) were synthesized. All compounds were fully characterized by analytical and spectroscopic techniques (IR, UV-Vis, NMR) and also by mass spectrometry. The solid state molecular structures of the complexes [Ru(η 6 -p-cymene)(Cl) (L 2 )], [Ru(η 6 -p-cymene)(Cl)(L 3 )] and [Ru(η 6 -p-cymene)(Cl)(L 4 )] revealed that the 2-aminofluorene and p-cymene moieties coordinate to ruthenium(II) in a three-legged piano-stool geometry. The synthesized complexes were used as catalysts for the dehydrogenative coupling of benzyl alcohol with a range of amines (aliphatic, aromatic and heterocyclic). The reactions were carried out under thermal heating, ultrasound and microwave assistance, using solvent or solvent free conditions, and the catalytic performance was optimized regarding the solvent, the type of base, the catalyst loading and the temperature. Moderately high to very high isolated yields were obtained using [Ru(η 6 -pcymene)(Cl)(L 4 )] at 1 mol%. In general, microwave irradiation produced better yields than the other two techniques irrespective of the nature of the substituents.

show abstract

Aerobic oxidative coupling of alcohols and amines towards imine formation by a dicopper(I,I) catalyst

Cited by 23 publications

References 98 publications

Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

Cuprophilic Interactions in and between Molecular Entities

Synthesis of Imines via Reactions of Benzyl Alcohol with Amines Using Half‐Sandwich (η⁶‐p‐cymene) Ruthenium(II) Complexes Stabilised by 2‐aminofluorene Derivatives

Contact Info

Product

Resources

About

Aerobic oxidative coupling of alcohols and amines towards imine formation by a dicopper(I,I) catalyst

Cited by 23 publications

References 98 publications

Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

Cuprophilic Interactions in and between Molecular Entities

Synthesis of Imines via Reactions of Benzyl Alcohol with Amines Using Half‐Sandwich (η6‐p‐cymene) Ruthenium(II) Complexes Stabilised by 2‐aminofluorene Derivatives

Contact Info

Product

Resources

About

Synthesis of Imines via Reactions of Benzyl Alcohol with Amines Using Half‐Sandwich (η⁶‐p‐cymene) Ruthenium(II) Complexes Stabilised by 2‐aminofluorene Derivatives