Domino Reactions Triggered by Hydroformylation

Petricci, Elena; Cini, Elena

doi:10.1007/128_2013_463

Cited by 18 publications

(10 citation statements)

References 77 publications

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“…The resulting keto‐FAME are then converted into amino derivatives by reductive amination . Concurrently to tandem metathesis/hydrogenation , one of the easiest way to access amino oleochemicals is undoubtedly hydroaminomethylation (HAM) . The HAM reaction has already been widely described and finds application in the synthesis of pharmaceuticals or natural compounds .…”

Section: Introductionmentioning

confidence: 99%

Hydroaminomethylation of oleochemicals: A comprehensive overview

Vanbésien

Nôtre²,

Monflier

et al. 2017

Euro J Lipid Sci & Tech

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The present review explores the historical background of the rhodium-catalyzed hydroaminomethylation (HAM) of vegetable oils and the recent developments in this field. The reaction conditions are especially discussed and commented upon. Various amines have been grafted onto alkyl chains of vegetable oils, thus giving rise to a wide range of bio-based HAM-products. A focus is on bifunctional HAM-products as they have potential as monomers in polymer chemistry. The nature of the ligands stabilizing the rhodium catalytic species is also discussed. The catalytic results obtained with phosphanes and amines are analyzed and compared. The goal of this review is to convince the reader that HAM of vegetable oils is a simple and effective synthetic pathway to access valuable functionalized bio-based compounds with industrial potential.Practical applications: Products resulting from hydroaminomethylation of vegetable oils have potential as monomers in polymer chemistry and as bio-based surface-active agents.

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Section: Introductionmentioning

confidence: 99%

Hydroaminomethylation of oleochemicals: A comprehensive overview

Vanbésien

Nôtre²,

Monflier

et al. 2017

Euro J Lipid Sci & Tech

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“…The most prominent tandem reaction incorporating hydroformylation as the initial reaction step is hydroaminomethylation (HAM). This three‐step auto‐tandem reaction consists of hydroformylation, in‐situ condensation of the intermediate aldehyde with an amine and final hydrogenation of the imine/enamine intermediate to a saturated amine (Scheme ) .…”

Section: Carbonylative Functionalizationmentioning

confidence: 99%

The mission of addition and fission – catalytic functionalization of oleochemicals

Seidensticker

Vorholt

Behr

2015

Euro J Lipid Sci & Tech

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Oleochemicals are used in the chemical industry in numerous processes and applications, having the largest share among all other renewable resources. Besides the well‐known transformations performed at the carboxylic moiety of the alkyl chain, many natural occurring fatty compounds offer a further opportunity for refinement, that is: catalytic functionalization of the CC double bond. In the present review, the authors describe the mission of the scientific work that is performed at the chair of Technical Chemistry at the TU Dortmund towards selective and atom economic functionalization of oleochemicals. Special emphasis lays on homogenous transition metal catalysis towards potential applications of the resulting products and their continuous production in miniplant scale. The given examples are discussed in the context of the work of other groups and summarize recent developments in the field of addition and fission reactions of oleochemicals. The Mission of Addition and Fission—The functionalization of oleochemicals using homogeneous transition metal catalysis is a very elegant way for producing valuable chemicals via many possible pathways. In this review, recent contributions to e.g. addition or cleavage reactions by Behr's group at the TU Dortmund are presented and discussed in the context of relevant literature, highlighting their significance in this important field of oleochemistry.

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“…[16] Tandem catalytic systems triggeredb yh ydroformylation for the transformation of olefins have emerged as ap owerful platform for developing ande xpanding tandem catalytic strategies,n ot least due to the versatile chemistry of the aldehyde moiety. [19][20][21][22] One of the most prominent examples for tandem reactions under hydroformylationc ondition is hydroaminomethylation (HAM). [23,24] In this three-step tandem reaction amines are formed from olefins,t ypically catalyzed by ligand modified rhodium catalysts (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Rhodium‐Catalyzed Bis‐Hydroaminomethylation of Linear Aliphatic Alkenes with Piperazine

et al. 2016

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An efficientp rotocolw as developed to prepare as erieso fd ialkylpiperazines via Rh-catalyzed bis-hydroaminomethylation of linear aliphatic alkenes with piperazine.T he well-known Rh/Biphephos catalytic system was applied, yielding the desired dialkylpiperazines within six tandemc atalytic steps,a lready at low catalyst loadings of 0.1mol%. Fort he model alkene 1-octene,g ood yields and linearities of 80% and 77:23, respectively,w ere achieved under optimized conditions.I nfluences on the catalytic system regarding n/iso ratio, possible side reactions and the reactionp ath are discussed on the basis of yield vs. time plots and parameter optimization. With the developedg eneral protocol, other linear, functionalized and branched substrates were effectively transformed to the corresponding linear N,Ndisubstituted piperazines.

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Domino Reactions Triggered by Hydroformylation

Cited by 18 publications

References 77 publications

Hydroaminomethylation of oleochemicals: A comprehensive overview

Hydroaminomethylation of oleochemicals: A comprehensive overview

The mission of addition and fission – catalytic functionalization of oleochemicals

Rhodium‐Catalyzed Bis‐Hydroaminomethylation of Linear Aliphatic Alkenes with Piperazine

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