X‐ray Structure of the Isodiazomethane Complex Cr(CO)5C≡N‐NH2and  [3+2]‐Cycloadditions to the Metallo‐Nitrile‐Imine [Cr(CO)5C≡N‐NH]–[1]

Fehlhammer, Wolf Peter; Schoder, Friedrich; Weinberger, Bernd; Stolzenberg, H.; Beck, Wolfgang

doi:10.1002/zaac.200900085

Cited by 7 publications

(4 citation statements)

References 87 publications

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“…However, the procedure was not reproducible, yields were low (42%) even at a small scale, and the product was predominantly amorphous, dark-colored, and difficult to handle. Later it was also detected as a transient intermediate by Weinberger and co-workers, during the reaction of complexes of the type [M(CO) 5 CNPPh 3 ] (M = Cr, Mo, W) with carbonyl compounds under strongly acidic conditions, giving N -isocyanoimine complexes. , Since then, several additional reports regarding the role of NIITP in organometallic chemistry have appeared, − including the X-ray characterization of the reagent and related complexes, but such records will not be discussed in the present compilation.…”

Section: Discovery and Early Applicationsmentioning

confidence: 92%

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

et al. 2020

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N-Isocyaniminotriphenylphosphorane (NIITP) is a functionalized isonitrile that has been extensively applied in a variety of organic reactions during the last two decades. This Review summarizes the most important applications in organic synthesis of this versatile reactant, with the focus posed on mechanistic and methodological aspects allowing the generation of molecular diversity. NIITP combines the reactivity of isonitriles with that of phosphoranes to enable chemical transformations employed in the construction of compound libraries. Here, we cover from the initial applications of NIITP in the Nef isocyanide reaction to further derivations that render a variety of heterocyclic scaffolds. The presence of the isonitrile moiety in this singular compound makes possible the double addition of nucleophiles and electrophiles, which followed by inter(intra)molecular aza-Wittig type transformations enable several multicomponent and tandem processes. In particular, we stress the impact of NIITP in oxadiazole chemistry, from the early two-component transformations to recent examples of multicomponent reactions that take place in the presence of suitable electrophiles. In addition, we briefly describe the role of NIITP chemistry in generating skeletal and conformational diversity in cyclic peptides. The reaction of NIITP with alkynes is thoroughly revised, with particular emphasis on silver-catalyzed processes that have been developed in the last years. Biomedicinal applications of some reaction products are also mentioned along with a perspective of future applications of this reactant.

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Section: Discovery and Early Applicationsmentioning

confidence: 92%

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

et al. 2020

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“…Its [3+2]‐cycloadditions with acetylenes, trifluoroacetonitrile, carbon disulfide and phenyl isocyanate along with further relations and derivations within these classes of compounds are discussed in Ref. 88b. …”

Section: Outlook Related [3+2]‐cycloaddition Reactions Within the mentioning

confidence: 99%

A Simple and Direct Method for the Palladium‐Catalyzed Oxidative Coupling of Unactivated Allylarenes with Classic Arenes

2014

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“…There is a review on stable nitrile imines 5b, and there are reports on the parent species HC≡N + –C – H 2 and H–C≡N + –N – H, which display a surprising stability in the gas phase [6, 7]. An overall view of their chemical ambience, derivation and interrelations also with isocyanides and isocyanide complexes has been presented recently 8.…”

Section: Introductionmentioning

confidence: 99%

Fixation of Metallo Nitrile Ylides and Metallo Nitrile Imines as Ligands in Transition Metal Complexes [1]

Völkl¹,

Achatz²,

Schoder³

et al. 2010

Zeitschrift anorg allge chemie

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1,3-Dipoles of the type metallo nitrile ylide and metallo nitrile imine were prepared by mono-α-deprotonation of CH-acidic {[W(CO) 5 CHCH 2 PPh 3 ]PF 6 , M(CO) 5 CNCH 2 CO 2 R (M = Cr, W; R = Me, Et), [Pt(Cl)(CNCH 2 CO 2 Et)(PPh 3 ) 2 ]BF 4 } and NH-acidic isocyanide complexes (Cr(CO) 5 CNNH 2 ) and were stabilized by coordination to a second transition metal complex fragment {Cr(CO) 5 , [M(CO) 5 ] + (M = Mn, Re), [FeCp(CO) 2 ] + , [Pt(Cl)(PR 3 ) 2 ] + (R = Et, Ph)}. All dinu-* Prof. Dr. W. P. Fehlhammer E-Mail: wpfehlhammer@gmx.de [a]1339 clear products 1-7, 10, and 11 are neutral species except [(Ph 3 P) 2 (Cl)Pt{μ 2 -CNCH(CO 2 Et)}Pt(Cl)(PPh 3 ) 2 ]BF 4 (8). Complex (OC) 5 W{μ 2 -CNCH(CO 2 Et)}Pt(Cl)(PEt 3 ) 2 (5b) was characterized by X-ray diffraction. Twofold deprotonation/platination to give (OC) 5 Cr{μ 3 -CNC(Ph)}[Pt(Cl)(PPh 3 ) 2 ] 2 (9) was achieved in the case of Cr(CO) 5 CNCH 2 Ph.

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X‐ray Structure of the Isodiazomethane Complex Cr(CO)₅C≡N‐NH₂and [3+2]‐Cycloadditions to the Metallo‐Nitrile‐Imine [Cr(CO)₅C≡N‐NH]^–[1]

Cited by 7 publications

References 87 publications

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

A Simple and Direct Method for the Palladium‐Catalyzed Oxidative Coupling of Unactivated Allylarenes with Classic Arenes

Fixation of Metallo Nitrile Ylides and Metallo Nitrile Imines as Ligands in Transition Metal Complexes [1]

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