A transition-metal-based method for 1,2-diamination of alkenes. Synthesis of cobalt dinitrosoalkanes from alkenes, nitric oxide, and (.eta.5-cyclopentadienyl)(nitrosyl)cobalt dimer and their reduction to primary vicinal diamines

Becker, Paul; Bergman, Robert G.

doi:10.1021/om50001a001

Cited by 56 publications

(20 citation statements)

References 1 publication

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“…207 In this case, in-situ reduction of the dinitrosoalkane ligands with LiAlH 4 generates the corresponding 1,2-diamines 294 in fair to excellent yield. Notably, Bergman found that the reaction of 291 is not restricted to norbornyl systems and indeed undergoes stereospecific addition to a range of di-, tri- and tetra-substituted aliphatic alkenes.…”

Section: Transition Metal-catalyzed Diaminationmentioning

confidence: 97%

Methods for direct alkene diamination, new & old

2012

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The 1,2-diamine moiety is a ubiquitous structural motif present in a wealth of natural products, including non-proteinogenic amino acids and numerous alkaloids, as well as in pharmaceutical agents, chiral ligands and organic reagents. The biological activity associated with many of these systems and their chemical utility in general has ensured that the development of methods for their preparation is of critical importance. While a wide range of strategies for the preparation of 1,2-diamines have been established, the diamination of alkenes offers a particularly direct and efficient means of accessing these systems. The purpose of this review is to provide an overview of all methods of direct alkene diamination, metal-mediated or otherwise.

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Section: Transition Metal-catalyzed Diaminationmentioning

confidence: 97%

Methods for direct alkene diamination, new & old

2012

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“…There are only few metal complexes containing two s-N coordinated C-nitroso groups and all of them are stabilized by a chelate system in some way. Vicinal dinitroso compounds s-N coordinated to the same metal atom via both NO functions are especially known for cobalt because of their application in organic synthesis, [26][27][28][29][30][31][32][33][34][35][36][37] but some examples with ruthenium 38, 39 or platinum 40 also exist. If the second C-NO unit is located not close enough other functional neighbors, 9 for example a deprotonated amino group, 41,42 are able to stabilize the chelate as well.…”

Section: Introductionmentioning

confidence: 99%

1,4-Bis(4-nitrosophenyl)piperazine: novel bridging ligand in dinuclear complexes of rhodium(iii) and iridium(iii)

2012

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The synthesis, spectroscopic characterization and crystal structures of the first 1,4-bis(4-nitrosophenyl)-piperazine (BNPP) (4) bridged dinuclear complexes of rhodium(III) and iridium(III) are presented. All new compounds were characterized by their NMR, IR and mass spectra. The X-ray structure analyses of the obtained half-sandwich complexes revealed a slightly distorted pseudo-octahedral configuration ("three-legged pianostool") for the metal(III) centers. The bridging BNPP ligand is s-N coordinated by both nitroso groups and shows different conformations of the piperazine ring depending on the solvent used for crystallization. Moreover the crystal structures of 1,4-bis(4-nitrosophenyl)piperazine (4) and its precursor 1,4-diphenylpiperazine (3) are reported.

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“…The overall transformation could also be used to generate 1,2-diamines if [CpCo{(NO) 2 (olefin)}] (42) was reacted with LiAlH 4 . Another interesting phenomenon is the decreasing stability of the resulting CpCo(I) complexes in dependence to the increasing number of hydrogens in α-position to the nitroso groups (Scheme 14) (Becker and Bergman 1983b).…”

Section: Phosphitesmentioning

confidence: 99%

The broad diversity of CpCo(I) complexes

Thiel

Hapke

2014

Reviews in Inorganic Chemistry

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AbstractThe presented review will focus on the systematic overview of the available synthetic approaches and the reactivity and the structural characteristics of selected mononuclear CpCo(I) complexes with (non)chelating neutral donor ligands. The complexes containing symmetrical or unsymmetrical neutral ligand combinations aside from the anionic cyclopentadienyl (Cp) ligand will be discussed and the differences to complexes with substituted Cp ligands will be considered in selected cases.

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A transition-metal-based method for 1,2-diamination of alkenes. Synthesis of cobalt dinitrosoalkanes from alkenes, nitric oxide, and (.eta.5-cyclopentadienyl)(nitrosyl)cobalt dimer and their reduction to primary vicinal diamines

Cited by 56 publications

References 1 publication

Methods for direct alkene diamination, new & old

Methods for direct alkene diamination, new & old

1,4-Bis(4-nitrosophenyl)piperazine: novel bridging ligand in dinuclear complexes of rhodium(iii) and iridium(iii)

The broad diversity of CpCo(I) complexes

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