Synthesis of organic heterocycles via multicomponent reactions with cyano transition metal complexes

Rieger, Dirk; Lotz, Sabine D.; Kernbach, Ulrich; André, Christoph; Bertran-Nadal, J.; Fehlhammer, Wolf Peter

doi:10.1016/0022-328x(94)05258-d

Cited by 43 publications

(16 citation statements)

References 53 publications

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“…[23][24][25][26][27] Complexes with amino-functionalized oxazolines have been derived from a three-component cycloaddition of an isocyanide (CNR 1 ) and a ketone (R 2 R 3 C᎐ ᎐ O) to ligated hydrogen isocyanide (M-CNH) to form a carbenoid C2-metal coordinated 4-amino-oxazoline (b) in various transition metal complexes [M{CNC(NHR 1 )C(R 2 )(R 3 )O}]. [28][29][30][31][32] In spite of the interest of the presence of the additional amino-group for subsequent reactivity, this route has not been explored further, conceivably on account of the difficulties normally associated with the synthesis of a well-defined CNH complex and the use of an isocyanide as the amino group source.…”

Section: Introductionmentioning

confidence: 99%

2-Amino-2-oxazoline and trialkylisourea Pt(ii) complexes derived from organocyanamides

Ferreira¹,

Silva

Michelin

et al. 2003

Dalton Trans.

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In the di(organocyanamide) complexes trans-[PtCl 2 (NCNR 2 ) 2 ] (R = Me 1a, Et 1b), prepared by reaction of PtCl 2 with the appropriate NCNR 2 , the cyanamide ligands, activated by coordination, undergo an unprecedented nucleophilic addition, at room temperature, of an haloalcohol (ClCH 2 CH 2 OH/LiBu n ) or of an alcohol (MeOH) to give theThe X-ray crystal structure of 2b is also reported, indicating a π-bond delocalization along the N ؒؒ ᎐C ؒؒ ᎐N group of the aminooxazoline ligands.

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Section: Introductionmentioning

confidence: 99%

2-Amino-2-oxazoline and trialkylisourea Pt(ii) complexes derived from organocyanamides

Ferreira¹,

Silva

Michelin

et al. 2003

Dalton Trans.

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“…Therein, NHC complexes were isolated as intermediates towards the generation of such heterocycles. 9,10 Building on this work, Ruiz et al 11 also reported multicomponent reactions. However, the main focus was on isolating the respective Mn heterocycle complexes.…”

Section: Manganese(i) Nhc Complexesmentioning

confidence: 76%

“…7 Scheme 2 Mn(I) oxazole and imidazole complexes generated by multi-component reactions. 9,10 Scheme 1 Synthesis of Mn(I) NHC compounds from P1 via Mn Fischer-type carbene complex P2 and the ketenimine route. 8 NHC complexes C5x and C6x (Scheme 3, where ''x'' represents a whole series of complexes).…”

Section: Manganese(i) Nhc Complexesmentioning

confidence: 99%

Group 7 transition metal complexes with N-heterocyclic carbenes

et al. 2013

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This tutorial review summarizes all works and highlights recent advances published in the growing field of group 7 N-heterocyclic carbene (NHC) complexes. It provides a valuable source for all scientists that are interested in conducting research with new compounds bearing these metals. The article provides an overview of all manganese NHC complexes that are known to date. There are a lot of examples where manganese NHC complexes show unpredicted behaviour during synthesis, very different from other transition metal NHC complexes and their higher homologues rhenium and technetium. These differences are depicted and discussed. Furthermore, the chemistry of technetium NHC compounds and their chemical behaviour are discussed. To date published work on technetium NHC chemistry has been restricted to the oxidation state +v. It was found that such compounds are very reactive but show great stability in dry air. Their radioactivity makes such compounds interesting candidates for radiochemical applications. Since most group 7 NHC chemistry was conducted on rhenium NHC complexes, this tutorial review highlights the chemical behaviour of such compounds. Rhenium(i) complexes reveal luminescent properties, making them interesting candidates for applications ranging from biological markers to organic light-emitting diodes (OLEDs). Another interesting feature is the radioactivity of some compounds, which makes them excellent candidates for radiopharmaceutical research; hence their synthesis and reactivity are discussed.

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“…Preparation of dimeric NHC iron complex starting from a sulfonium salt precursor. [91- Fehlhammer et al have expanded this method towards monometallic complexes starting from (iso)cyanide metal precursors [86,87]. Their approach is based on treament of the benzonitrile complex [CpFe(CNPh)(CO) 2 ]PF 6 with aziridine and tetrabutylammonium bromide [86].…”

mentioning

confidence: 99%

“…Their approach is based on treament of the benzonitrile complex [CpFe(CNPh)(CO) 2 ]PF 6 with aziridine and tetrabutylammonium bromide [86]. As an extension of this approach, multicomponent reactions starting from cyanide complex 26, an aldehyde, an isocyanide and an ammonium or anilinium salt affords piano-stool NHC iron complexes (Scheme 11) [87]. Both monocarbene(27) and biscarbene(28)complexes are accessible as a result of the two available cyanide ligands.…”

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confidence: 99%

Piano-stool N-heterocyclic carbene iron complexes: Synthesis, reactivity and catalytic applications

Johnson

Albrecht

2017

Coordination Chemistry Reviews

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This review summarises the advances of N-heterocyclic carbenes (NHCs) as ligands to iron half-sandwich complexes, often referred to as piano-stool complexes because of their structural motif. The review introduces various synthetic routes towards this sub-class of NHC iron-complexes including in particular direct and transmetallation strategies as well as the synthesis of the carbene directly within the iron coordination sphere. Many of these complexes have demonstrated promising reactivity that is relevant to the arenas of catalysis and materials chemistry. In particular, bond activation (e.g. C-H, Si-H, H-H) processes provide exciting new opportunities to exploit these systems for stoichiometric and catalytic transformations. Substantial advances have been achieved specifically in the catalytic reduction of unsaturated substrates, and this topic is emphasised in particular.

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Synthesis of organic heterocycles via multicomponent reactions with cyano transition metal complexes

Cited by 43 publications

References 53 publications

2-Amino-2-oxazoline and trialkylisourea Pt(ii) complexes derived from organocyanamides

2-Amino-2-oxazoline and trialkylisourea Pt(ii) complexes derived from organocyanamides

Group 7 transition metal complexes with N-heterocyclic carbenes

Piano-stool N-heterocyclic carbene iron complexes: Synthesis, reactivity and catalytic applications

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