Iron Catalyzed Synthesis of Pyrimidines Under Air

Mondal, Rakesh; Sinha, Suman; Das, Siuli; Chakraborty, Gargi; Paul, Nanda D.

doi:10.1002/adsc.201901172

Cited by 65 publications

(20 citation statements)

References 56 publications

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“…Paul and co‐workers established an iron catalysed one‐pot synthesis of 2,4,6‐trisubstituted pyrimidines. [ 79 ] The dehydrogenative coupling reaction between primary 138 and secondary alcohols 137 with amidines 139 generated 2,4,6‐trisubstituted pyrimidines 140 (Scheme 53). The optimised condition for this reaction includes 0.5 equiv.…”

Section: Classificationmentioning

confidence: 99%

Recent advances in the iron‐catalysed multicomponent reactions

Saranya

Aneeja

Neetha

et al. 2020

Applied Organom Chemis

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Iron‐catalysed reactions are widely used in organic synthesis owing to its benefits over other metals. Among the important organic reactions, multicomponent reactions play a significant role due to its greener aspects like high atom economy, minimal amount of by‐product, economic feasibility etc. For the past few years, iron‐catalysed multicomponent reactions have attracted the attention of several chemists which lead to the invention of some fine chemistry. The majority of iron‐catalysed multicomponent reactions results in the synthesis of heterocyclic compounds having biologically active natural products, pharmaceutical etc. These developments in the iron‐catalysed multicomponent reactions are the focus of this review. This is the first review in this topic which covers the literature up to 2020, and it encompasses the different methods for the synthesis of acyclic, carbocyclic and heterocyclic compounds.

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Section: Classificationmentioning

confidence: 99%

Recent advances in the iron‐catalysed multicomponent reactions

Saranya

Aneeja

Neetha

et al. 2020

Applied Organom Chemis

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“…The air-stable iron complex Fe-3 promoted the multicomponent dehydrogenative functionalization of alcohols to form 2,4,6-trisubstituted pyrimidines (Scheme 28c). [47] The iron(II)-complex, featuring a redox noninnocent 2-phenylazo-(1,10-phenanthroline) ligand enabled the synthesis at moderate reaction temperatures with a substoichiometric amount of base in air. The metal-ligand cooperative mechanism was proposed to feature an azo-anion radical iron(II) species as the active catalyst for the one-electron hydrogen atom transfer process to form a ketyl radical intermediate.…”

Section: Pyrimidinesmentioning

confidence: 99%

“…The metal-ligand cooperative mechanism was proposed to feature an azo-anion radical iron(II) species as the active catalyst for the one-electron hydrogen atom transfer process to form a ketyl radical intermediate. [47] Recently a comparative study of nickel-catalyzed dehydrogenative formation of pyrimidines was reported (Scheme 28d). [48] The two catalyst systems are operating in two different pathways.…”

Section: Pyrimidinesmentioning

confidence: 99%

Borrowing Hydrogen and Acceptorless Dehydrogenative Coupling in the Multicomponent Synthesis of N‐Heterocycles: A Comparison between Base and Noble Metal Catalysis

Hofmann

Hultzsch

2021

Eur J Org Chem

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In memory of Klaus HafnerAcceptorless dehydrogenative coupling reactions (ADC) and hydrogen transfer strategies (HT) provide a powerful tool in the multicomponent formation of N-heterocycles. A broad variety of complex products can be obtained starting from simple, cheap and commercially available reagents. The protocols are highly atom-efficient, as water, dihydrogen, or in some cases hydrogen peroxide, are the only by-products. Moreover, neither further reducing or oxidizing agents, nor external hydrogen are in general required. Especially base metal-catalyzed strategies become ever more important. Therefore, in recent years, various different manganese, iron, cobalt, nickel and copper catalysts have been developed. This Minireview highlights the progress that has been made by using abundant metal complexes to promote multicomponent cyclizations for the formation of Nheterocycles and compares their performance with available noble metal catalyst systems.

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“…Very recently , Paul and co‐workers [91] have introduced redox‐active iron(II) complex ( Fe‐4 , 3 mol%) for the synthesis of pyrimidines ( 98 ) via coupling of guanidine ( 97 ), primary alcohols ( 1 a ) and secondary alcohols ( 1 ) in the presence of relatively low base loading (KO t Bu 0.5 equiv.) and at 100 °C (Scheme 44).…”

Section: Synthesis Of Aromatic Heterocycles Via Catalytic De(hydrogenation)mentioning

confidence: 99%

Recent Progress in the Synthesis of Heterocycles through Base Metal‐Catalyzed Acceptorless Dehydrogenative and Borrowing Hydrogen Approach

et al. 2021

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Development in the area of acceptorless dehydrogenation (AD) and borrowing hydrogen (BH) catalysis emerge as one of the potential tools for various CÀ C and C-heteroatom bond forming reactions. Alcohols, which are important lignocellulosic biomass products, act as pivotal electrophilic coupling partners in such processes and interestingly only H 2 or H 2 O is eliminated as a byproduct. Initially, the area was developed by the use of noble metal catalysts. Recently, base metals such as Mn, Fe, Co, and Ni proved to be environmentally benign and inexpensive alter-natives for the noble metals in the application of AD and BH methods. This transition metal catalyzed AD and BH approaches also allow access toward a plethora of structurally important heterocyclic molecules via environmentally benign and atom economical strategy. Herein, we summarize the current and rising expansion of base metal catalyzed heterocycles synthesis through acceptorless dehydrogenation and borrowing hydrogenation strategy.

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Iron Catalyzed Synthesis of Pyrimidines Under Air

Cited by 65 publications

References 56 publications

Recent advances in the iron‐catalysed multicomponent reactions

Recent advances in the iron‐catalysed multicomponent reactions

Borrowing Hydrogen and Acceptorless Dehydrogenative Coupling in the Multicomponent Synthesis of N‐Heterocycles: A Comparison between Base and Noble Metal Catalysis

Recent Progress in the Synthesis of Heterocycles through Base Metal‐Catalyzed Acceptorless Dehydrogenative and Borrowing Hydrogen Approach

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