Transition Metal Complexes of Diazenes. 35. Synthesis of 1-(Arylamino)indoles by Rhodium-Catalyzed Addition of Alkynes to 1,2-Diaryldiazenes

Aulwurm, Uwe R.; Melchinger, J. U.; Kisch, Horst

doi:10.1021/om00007a045

Cited by 71 publications

(19 citation statements)

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“…[12] However, the current methodology also suffers from some limitations. [12] However, the current methodology also suffers from some limitations.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

A General Method to Diverse Cinnolines and Cinnolinium Salts

Zhao

Huang

et al. 2013

Chemistry A European J

132

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“…[12] However, the current methodology also suffers from some limitations. [12] However, the current methodology also suffers from some limitations.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

A General Method to Diverse Cinnolines and Cinnolinium Salts

Zhao

Huang

et al. 2013

Chemistry A European J

132

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“…These hexacoordinate Ir III and Rh III compounds contain an orthometalated azobenzene or arylimine ring and two phosphane ligands in trans position, and were isolated during our work on the mechanism of the rhodium-catalyzed synthesis of indoles from 1,2-diaryldiazenes and alkynes. [6] The recently published survey of the Cambridge Crystallographic Database revealed that several complexes contain unfurcated MH´´´HC bonds with distances of 1.5 ± 2.2 (Scheme 1, type A,).…”

mentioning

confidence: 99%

Weak M-H⋅⋅⋅H-C and M-Cl⋅⋅⋅H-C Interactions in Orthometalated Iridium and Rhodium Complexes

et al. 1998

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Four different types of intramolecular MX´´´HC interactions have been observed in a series of five, structurally very similar, orthometalated iridium(iii) and rhodium(iii) complexes. For X H and M Ir or Rh, two-center or three-center interactions with MH´´´HC distances of 1.80 ± 1.83 (M Ir) or 2.00 ± 2.20 (M Rh) were observed. For X Cl the MCl´´´HC distances of the three-center arrangement (M Ir) were in the range of 2.38 ± 2.60 , while values of 2.41 ± 2.89 were found for the four-center geometry (M Rh). These weak interactions open new perspectives for the mechanism of cyclometalations.

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“…[24] The apparent lack of [3 + 2] reactivity with aromatic ketones and N-substituted imines was quite intriguing, since these substrates have been reported to undergo several catalytic tandem CÀH bond activation/ alkyne insertion processes. [2,[25][26][27] This seemingly unique reactivity of N-unsubstituted ketimines could result from facile formation of a ketimine-Rh I s complex, [28] or from formation of a Rh I -iminyl complex. Either complex may serve as a reactive intermediate to facilitate the activation of aromatic C À H bonds.…”

Section: Resultsmentioning

confidence: 99%

Tertiary Carbinamine Synthesis by Rhodium‐Catalyzed [3+2] Annulation of N‐Unsubstituted Aromatic Ketimines and Alkynes

Sun

Chen

Zhao

2010

Chemistry A European J

159

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A convenient and waste-free synthesis of indene-based tertiary carbinamines by rhodium-catalyzed imine/alkyne [3+2] annulation is described. Under the optimized conditions of 0.5-2.5 mol % [{(cod)Rh(OH)}(2)] (cod=1,5-cyclooctadiene) catalyst, 1,3-bis(diphenylphosphanyl)propane (DPPP) ligand, in toluene at 120 degrees C, N-unsubstituted aromatic ketimines and internal alkynes were coupled in a 1:1 ratio to form tertiary 1H-inden-1-amines in good yields and with high selectivities over isoquinoline products. A plausible catalytic cycle involves sequential imine-directed aromatic C-H bond activation, alkyne insertion, and a rare example of intramolecular ketimine insertion into a Rh(I)-alkenyl linkage.

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Transition Metal Complexes of Diazenes. 35. Synthesis of 1-(Arylamino)indoles by Rhodium-Catalyzed Addition of Alkynes to 1,2-Diaryldiazenes

Cited by 71 publications

References 0 publications

A General Method to Diverse Cinnolines and Cinnolinium Salts

A General Method to Diverse Cinnolines and Cinnolinium Salts

Weak M-H⋅⋅⋅H-C and M-Cl⋅⋅⋅H-C Interactions in Orthometalated Iridium and Rhodium Complexes

Tertiary Carbinamine Synthesis by Rhodium‐Catalyzed [3+2] Annulation of N‐Unsubstituted Aromatic Ketimines and Alkynes

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