Coupling Reactions of Zirconate Complexes Induced by Carbonyl Compounds

Xi, Chanjuan; Yan, Xiaoyu; You, Wei; Takahashi, Tamotsu

doi:10.1002/ange.200904255

Cited by 2 publications

(1 citation statement)

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“…diene complexes 2 and the allenyl-aza-zirconacycles 3 were thus generated in high yields from tBuCN, a different nitrile RCN, a Si-tethered diyne, and the zirconocene species. [14][15][16][17] We believe that these two reactive organometallic intermediates 2 and 3 should be synthetically useful for the synthesis of heterocyclic compounds. Indeed in this work, as shown in Scheme 2, further reactions of these intermediates with nitriles were found to proceed smoothly through interesting insertions and skeletal rearrangements, providing useful synthetic methods for N-containing heterocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Selective Syntheses of 5‐Azaindoles through Zirconocene‐Mediated Multicomponent Reactions with Three Different Nitrile Components and One Alkyne Component

Zhang

Zhao

et al. 2011

Chemistry A European J

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5-Azaindoles either with three different substituents at their 2-, 4-, and 6-positions or with two identical substituents at their 2- and 6-positions and a different one at the 4-position, were obtained in good to excellent isolated yields by a zirconocene-mediated multicomponent process. Each reaction involved four organic partners, comprising a Si-tethered diyne, one tBuCN component, and two (either different or identical) nitriles. All these four components were combined through the action of a Cp(2)Zr(II) species into a three-ring fused Zr/Si-containing organometallic complex in a perfectly chemo- and regioselective manner. This multicomponent reaction process consisted of three reaction steps, all of which were made clear through the isolation and characterization of their corresponding organometallic intermediates: the zirconacyclopropene-azasilacyclopentadienes 2, the allenyl-aza-zirconacycles 3, and the three-ring fused complexes 6. X-ray single-crystal structural analyses of two three-ring fused Zr/Si-containing intermediates and two 5-azaindoles unambiguously showed the positions of the different substituents and the regioselectivity. Iminopyrrole derivatives could be also highly selectively prepared from a Si-tethered diyne and two different nitriles.

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Section: Introductionmentioning

confidence: 99%