Photochemie von acetylenen in gegenwart von metallcarbonylen I

Kolshorn, Heinz; Meier, Herbert; Müller, Eu.

doi:10.1016/s0040-4039(01)96986-2

Cited by 8 publications

(2 citation statements)

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“…In line with this latter approach, we report herein the first efficient synthesis and full characterization of [bis(hexamethylene)cyclopentadienone]iron tricarbonyl ( 1 b ; Figure B), a Knölker‐type complex that features cyclooctene rings fused to the 2,3‐ and 4,5‐positions of the cyclopentadienone ring, and its application as a precatalyst for the reduction of C=O bonds.…”

Section: Introductionmentioning

confidence: 64%

“…Then, a second elimination reaction in the presence of lithium diisopropylamide (LDA) allows the desired product 4 to be obtained. According to previous reports, if 4 was reacted with Ni, W, Co, and Fe carbonyl complexes, several products were isolated, among which were, in the case of Fe, substantial amounts of tris(hexamethylene) benzene ( 5 ; derived from cyclotrimerization) and minor quantities of 1 b (Scheme ). This peculiar behavior caught our attention and induced us to investigate the reaction to optimize the formation of 1 b .…”

Section: Resultsmentioning

confidence: 96%

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Synthesis of [Bis(hexamethylene)cyclopentadienone]iron Tricarbonyl and its Application to the Catalytic Reduction of C=O Bonds

et al. 2017

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Herein, we report the synthesis of [bis(hexamethylene)cyclopentadienone]iron tricarbonyl (1 b) by the reaction of cyclooctyne with Fe(CO)5 and the investigation of its catalytic properties in C=O bond reduction. As a result of the peculiar reactivity of cyclooctyne, 1 b was formed in good yield (56 %) by intermolecular cyclative carbonylation/complexation with Fe(CO)5. Compound 1 b was characterized fully and its crystal structure was determined by using XRD. Catalytic tests revealed that, upon in situ activation with Me3NO, 1 b promotes the hydrogenation of ketones, aldehydes, and activated esters as well as the transfer hydrogenation of ketones and shows a higher activity than the classical “Knölker complex” (1 a). Studies on the hydrogenation kinetics in the presence of 1 a and 1 b (respectively) suggest that this difference in activity is probably caused by the better stability of the 1 b‐derived complex than that of the in situ generated Knölker–Casey catalyst.

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Section: Introductionmentioning

confidence: 64%

Section: Resultsmentioning

confidence: 96%