A General and Selective Iron‐Catalyzed Aminocarbonylation of Alkynes: Synthesis of Acryl‐ and Cinnamides

Driller, Katrin Marie; Prateeptongkum, Saisuree; Jackstell, Ralf; Beller, Matthias

doi:10.1002/anie.201005823

Cited by 112 publications

(32 citation statements)

References 112 publications

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“…They are inexpensive, environmentally friendly, and relatively non-toxic. However, few examples exist of their applications in carbonylative reactions [11][12][13][14][15] . The main reasons are: (i) the high affinity of CO with iron which make the metal center saturately coordinated and then activity inhibited; (ii) the decreased ability of copper catalyst in the oxidative addition step and also the low stability of carbonyl-copper intermediates.…”

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confidence: 99%

Copper/iron co-catalyzed alkoxycarbonylation of unactivated alkyl bromides

2018

Commun Chem

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Carbonylative transformations of alkyl bromides have been explored less than those of aryl halides, in part because of the high barrier to activation of aryl bromides. Additionally, alkylmetal reagents formed in situ can tend to undergo β-hydride elimination. Here we describe a copper/iron co-catalyzed alkoxycarbonylation of unactivated alkyl bromides. In the presence of catalytic quantities of iron and copper catalysts, primary, secondary, and tertiary alkyl bromides are carbonylatively transformed into the corresponding aliphatic esters in good yields. A potential reaction mechanism is proposed based on control experiments.

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confidence: 99%

Copper/iron co-catalyzed alkoxycarbonylation of unactivated alkyl bromides

2018

Commun Chem

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“…In 2011, Beller and co‐workers demonstrated that the combination of Fe 3 (CO) 12 as a catalyst and 32 as the ligand was an efficient system for the aminocarbonylation of alkynes with amines and carbon monoxide (10 bar) (Scheme ) . In this approach, aminocarbonylation of phenylacetylene smoothly proceeded with various aliphatic primary and secondary amines, thereby giving the corresponding E ‐configured N ‐substituted cinnamide derivatives in good to high yields.…”

Section: Synthesis Of Amides From Alkynesmentioning

confidence: 99%

Recent Advances in the Functionalization of Hydrocarbons: Synthesis of Amides and its Derivatives

Reddy

Lima

2019

Asian J Org Chem

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The functionalization of hydrocarbons represents an attractive approach for the synthesis of amides. The amide bond is one of the most fascinating functional groups in nature, owing to its high bond polarity, stability, and conformational diversity. Amides play an essential role in the composition of many natural products, agrochemicals, peptides, polymers, proteins, biologically active systems, and functional materials. The present review focuses on recent breakthroughs and current challenges for the functionaliza-tion of hydrocarbons to synthesize amides. This review provides comprehensive coverage on recent reports of various efficient metal-catalyzed and metal-free methods for the synthesis of amides from hydrocarbons (such as methylarenes, alkenes, and alkynes). We also show the reaction mechanisms of representative reactions in a detailed way with numerous examples and applications of these methods in the synthesis of bioactive compounds.

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“…[7] Since the original work of Reppe in the past century, [8] carbonylation of alkynes with various nucleophiles such as H 2 O, [9] alcohols (O nucleophiles), [10] thiols (S nucleophiles), [11] and amines (N nucleophiles) [12] have been extensively studied and numerous catalysts are available for producing all kinds of carbonyl compounds.I nc ontrast, the use of Cnucleophiles,w hich create synthetically important ketones,has been investigated to alesser extent. [7] Since the original work of Reppe in the past century, [8] carbonylation of alkynes with various nucleophiles such as H 2 O, [9] alcohols (O nucleophiles), [10] thiols (S nucleophiles), [11] and amines (N nucleophiles) [12] have been extensively studied and numerous catalysts are available for producing all kinds of carbonyl compounds.I nc ontrast, the use of Cnucleophiles,w hich create synthetically important ketones,has been investigated to alesser extent.…”

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Markovnikov‐Selective Palladium Catalyst for Carbonylation of Alkynes with Heteroarenes

Liu

Dühren

et al. 2017

Angew Chem Int Ed

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A new class of palladium catalysts, based on heterocyclic diphosphines, was rationally designed and synthesized. Application of one of these catalysts allows novel Markovnikov-selective carbonylation of non-activated alkynes with heteroarenes to give the corresponding branched α,β-unsaturated ketones in excellent yields (up to 97 %) and regioselectivities (b/l up to 99:1). In addition to heteroarenes, other common nucloephiles (alcohol, phenol, amine, and amide) furnish the desired carbonylation products smoothly in high yields.

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A General and Selective Iron‐Catalyzed Aminocarbonylation of Alkynes: Synthesis of Acryl‐ and Cinnamides

Cited by 112 publications

References 112 publications

Copper/iron co-catalyzed alkoxycarbonylation of unactivated alkyl bromides

Copper/iron co-catalyzed alkoxycarbonylation of unactivated alkyl bromides

Recent Advances in the Functionalization of Hydrocarbons: Synthesis of Amides and its Derivatives

Markovnikov‐Selective Palladium Catalyst for Carbonylation of Alkynes with Heteroarenes

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