One-Pot Synthesis of Secondary and Tertiary Amines by Carbonylative Hydroaminomethylation of Alkenes Catalyzed by Di(μ-chloro)bis(η4-1,5-cyclooctadiene)dirhodium

Rische, Thorsten; Eilbracht, Peter

doi:10.1055/s-1997-1338

Cited by 78 publications

(31 citation statements)

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“…For instance, aliphatic terminal olefins such as 1-octene, 1-dodecene, 1-tetradecene, 1-hexadecene, and 1-octadecene are hydroaminomethylated with morpholine by using a [{RhCl(cod)} 2 ] catalyst to form mixtures of the corresponding linear and branched amines. [44] On the other hand, in the presence of phosphane ligands, for example, xantphos derivatives, highly regioselective and efficient hydroaminomethylations are achieved. [45] Good n:iso ratios (up to 10:1) have been observed for the hydroaminomethylation of the functionalized olefin 3,3-dimethylpent-4-ene-2-one with secondary amines by using phosphane-free rhodium catalysts.…”

Section: Hydroaminomethylationmentioning

confidence: 99%

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

et al. 2004

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The regioselective functionalization of terminal alkenes and alkynes is of utmost importance for the synthesis of a wide variety of organic products. Based on the original observation by Vladimir Markovnikov-the pioneer of this field of research-in the 19th century, the possible regioisomeric products are classified as Markovnikov or anti-Markovnikov products. Contrary to traditional belief, it is nowadays possible to control the regiochemistry of various additions of nucleophiles to alkenes and alkynes by applying different transition-metal catalysts. Recent developments in this area of selective functionalization of alkenes and alkynes are reviewed.

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Section: Hydroaminomethylationmentioning

confidence: 99%

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

et al. 2004

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“…For this transition metal-catalyzed tandem reaction a catalyst based on [Rh(cod)Cl] 2 was employed which showed high activities in reported hydroaminomethylation reactions [33][34][35][36][37][38][39][40]. In Figure 3.…”

Section: Resultsmentioning

confidence: 99%

Hydroaminomethylation of the Renewable Limonene with Ammonia in an Aqueous Biphasic Solvent System

Behr

Wintzer

2015

Chem Eng & Technol

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With the hydroaminomethylation of the natural compound limonene with ammonia an atom-economic method for the synthesis of primary amines is described. This tandem reaction allows the direct conversion of the unfunctionalized monoterpene to a valuable amine product. For the first time, ammonia served as substrate to result in a maximum primary amine yield of 25 %. To overcome unwanted side reactions, a biphasic solvent system was used, consisting of an aqueous catalyst phase and an organic product phase. As catalyst the water-soluble transition metal complex [Rh(cod)Cl] 2 /triphenylphosphine trisulfonate was chosen. In combination with the surfactant hexadecyltrimethylammonium chloride it provided a good phase interaction and the possibility for easy phase separation after the reaction.

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“…So wurden neben Standardolefinen [19] auch funktionalisierte Alkene [20,21], einfache [22] und funktionalisierte terminale Diolefine [23] sowie Nitroverbindungen [24] erfolgreich in der Hydroaminomethylierung eingesetzt. Ferner wurde eine Variante entwickelt, symmetrisch und unsymmetrisch substituierte Amine zu synthetisieren [25], welche bis dahin nur schwer zugänglich waren.…”

Section: Problemstellungunclassified

Katalytische Hydroaminomethylierung für die hochselektive Synthese von linearen Fettaminen

Buch

Jackstell

Bühring

et al. 2007

Chemie Ingenieur Technik

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One-Pot Synthesis of Secondary and Tertiary Amines by Carbonylative Hydroaminomethylation of Alkenes Catalyzed by Di(μ-chloro)bis(η4-1,5-cyclooctadiene)dirhodium

Cited by 78 publications

References 0 publications

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

Hydroaminomethylation of the Renewable Limonene with Ammonia in an Aqueous Biphasic Solvent System

Katalytische Hydroaminomethylierung für die hochselektive Synthese von linearen Fettaminen

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