Journal ArticleDOI
A Review of the Selective Catalytic Reduction of Aromatic Nitro Compounds into Aromatic Amines, Isocyanates, Carbamates, and Ureas Using CO.
Ahmed M. Tafesh,Jens Weiguny +1 more
TLDR
The use of CO as a reductant had been in the past confined to few reactions, but its use in organic synthesis, especially in the reductive carbonylation of nitro aromatics and the oxidative carbonylations of aromatic amines, has increased dramatically as mentioned in this paper.Abstract:
Although the use of CO as a reductant had been in the past confined to few reactions, its use in organic synthesis, especially in the reductive carbonylation of nitro aromatics and the oxidative carbonylation of aromatic amines, has increased dramatically. Since the discovery of CO-induced reduction of nitro groups, there has been a wide spread increase of interest in the application and mechanistic understanding of this reaction. In a major review published in 1988 it was noted, that in practice no studies of the mechanism of N-carbonylation of aromatic nitro compounds with alcohols leading to carbamates have been carried out. This review clearly shows a major change since that publication. Indeed, metal-catalyzed reductive carbonylation of nitro aromatics using CO as reducing agent has been in the past 10 years the subject of intense investigation both in academia and in the chemical industry. Several articles and reviews have covered the subject up to the late 1980s. The authors will concentrate on more recent literature, but sometimes older data will be used to establish an understanding of these reactions. 127 refs.read more
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Journal ArticleDOI
Synthesis of β-amino alcohols using the tandem reduction and ring-opening reaction of nitroarenes and epoxides
TL;DR: In this paper, a high yield one-pot synthesis of β-amino alcohols from nitroarenes and 1,2-epoxides was developed, which utilizes inexpensive iron dust as a reducing agent and NH 4 Cl as the only additive in a 50% (v/v) ethanol solution.
Journal ArticleDOI
CuSe2/CeO2 as a novel heterogeneous catalyst for reductive carbonylation of nitroarenes for generating urethanes
Abstract: The reaction of CuCl2, SeO2, and cetyltrimethylammonium bromide (CTAB) under the CO pressure in methanol produce a black solid, which is identified as cupric diselenide, CuIISe2 using various spectroscopic analyses. Impregnation of 5 wt% of CuSe2 onto CeO2 resulted in much more enhanced catalytic activity due to the uniform and highly dispersed particle. The reductive carbonylation of nitrobenzene (NB) as a model substrate has been examined in the presence of the CuSe2/CeO2 as a single component heterogeneous catalyst, which is found to exhibit excellent catalytic activity for generating methyl-N-phenyl carbamate (MPC) in a highly selective fashion. The effects of various reaction parameters such as temperature, pressure, and reaction time have been investigated. A plausible reaction mechanism using this cheap heterogeneous catalyst is also presented, especially invoking the importance of CuSe2(μ-CO) species.
Journal ArticleDOI
“Urea to urea” approach: access to unsymmetrical ureas bearing pyridyl substituents
TL;DR: In this article , a protocol for the synthesis of unsymmetrical ureas substituted by pyridyl/quinolinyl moiety has been developed, which concluded in metal-and base-free reamination of N,N-dimethyl-N‘-hetaryl Ureas with a wide range of aryl and alkyl amines.
Journal ArticleDOI
Metal-free Carbon Monoxide (CO) Capture and Utilization: Formylation of Amines
TL;DR: In this article, the capture and utilization of CO by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) were performed in the absence of transition-metal complexes.
Patent
Synthesis of a bruton?s tyrosine kinase inhibitor
Cyril Benhaim,Chen Wei,Erick Goldman,Andras Horvath,Philip Pye,Mark Stephen Smyth,Erik Verner +6 more
TL;DR: In this paper, the synthesis of Bruton's tyrosine kinase (Btk) inhibitor 1-((R)-3-(4-amino-3 -(4-phenoxyphenyl)- 1H-pyrazolo [3,4-d]pyrimidin-1-yl)piperidin]-prop-2-en-one
References
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Journal ArticleDOI
Water-Soluble Ligands, Metal Complexes, and Catalysts: Synergism of Homogeneous and Heterogeneous Catalysis
TL;DR: Water-soluble catalysts as mentioned in this paper combine the advantages of homogeneous and heterogeneous catalysis: simple and complete separation of the product from the catalyst, high activity, and high selectivity.
Journal ArticleDOI
Transformations of Chloroarenes, Catalyzed by Transition-Metal Complexes
Vladimir V. Grushin,Howard Alper +1 more
Journal ArticleDOI
Palladium(II) catalysts for living alternating copolymerization of olefins and carbon monoxide
TL;DR: In this article, the synthesis of well-defined Pd(II) catalysts that operate in aprotic solvents to yield living alternating copolymers of olefins and CO was reported.
Journal ArticleDOI
Palladium Complex-Catalyzed Reductive N-Heterocyclization of Nitroarenes: Novel Synthesis of Indole and 2H-Indazole Derivatives
TL;DR: The dichlorobis(triphenylphosphine)palladium (PdCl 2 (PPh 3 ) 1 )-tin(II) chloride (SnCl 2 ) system showed high catalytic activity for the reductive N-heterocyclization of various 2-nitrostyrene and N-(2-nitrobenzylidene)amine derivatives when employed at 100 o C for 16 h under 20 kg cm -2 of initial carbon monoxide pressure, to give the corresponding indole and 2H-indazole derivatives in
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