Unexpected transfer hydrogenation of C–C-double bonds during Tandem-RCM-isomerization reactions

Schmidt, Bernd; Staude, Lucia

doi:10.1016/j.jorganchem.2006.07.011

Cited by 16 publications

(11 citation statements)

References 31 publications

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“…The starting materials required for this route -the 2-substituted 2,3-dihydrofurans 12 -were synthesized from the diallyl ethers 11 by the tandem RCM/isomerization sequence. As we have previously reported, ethyl vinyl ether is the best additive for this particular ring size, because competing transfer hydrogenation [47] is excluded. [22] The diallyl ethers 11a-d were thus treated with the first-generation Grubbs catalyst A.…”

Section: Resultsmentioning

confidence: 57%

Ru‐ and Pd‐Catalysed Synthesis of 2‐Arylfurans by One‐Flask Heck Arylation/Oxidation

Schmidt¹,

Geißler²

2011

Eur J Org Chem

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Abstract2,5‐Disubstituted furans were synthesized by one‐flask Heck arylation/oxidation sequences. The starting materials are 2‐substituted 2,3‐dihydrofurans, conveniently available by RCM/isomerization sequences, and arenediazonium salts. These react in ligand‐free Heck reactions to afford 2,5‐disubstituted 2,5‐dihydrofurans, which are oxidized to the corresponding furans without isolation or intermediate workup. The oxidation is conveniently achieved with chloranil or DDQ, depending on the substrate.

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Section: Resultsmentioning

confidence: 57%

Ru‐ and Pd‐Catalysed Synthesis of 2‐Arylfurans by One‐Flask Heck Arylation/Oxidation

Schmidt¹,

Geißler²

2011

Eur J Org Chem

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“…For small organic molecules on the other hand such isomerization reactions were already studied in more detail. [38,39] For instance, it could be shown that phenylphosphoric acid can be used as an additive for the second generation Grubbs catalyst in order to prevent these isomerizations leading only to the desired metathesis products instead. [40,41] Having oligomer 3 identified we can assume that with lower amounts of MA present more self-metathesis reactions between terminal olefins can occur and higher molecular weight branched products are thus formed.…”

Section: Resultsmentioning

confidence: 99%

Acyclic Triene Metathesis Polymerization with Chain‐Stoppers: Molecular Weight Control in the Synthesis of Branched Polymers

Fokou

Meier

2008

Macromol. Rapid Commun.

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The synthesis of branched macromolecules from renewable resources via olefin metathesis is described. We observed that it is possible to control the molecular weight during the acyclic triene metathesis (ATMET) of a triglyceride by the application of methyl acrylate as a chain stopper for this straightforward one step one pot polymerization. The resulting branched materials were characterized by GPC, NMR as well as ESI‐MS and the combination of these techniques provided valuable insights into the polymer structure as well as occurring side reactions during this olefin metathesis polymerization reaction.magnified image

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“…Occasionally, difficulties arising from undesired transfer hydrogenation reactions were observed when conducting tandem RCM/isomerization reactions with unprotected alcohols. [52] Therefore, 10 was protected as a benzyl ether 11 (Scheme 2). Scheme 2.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 3‐Deoxy Glycals via Tandem Metathesis Sequences and Their Use in an Intermolecular Heck Arylation

Schmidt

Biernat

2008

Eur J Org Chem

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Deoxy glycals can be synthesized from a mannitol-derived C 2 -symmetric diene diol by using the tandem RCM/isomerization approach. Incorporation of a ruthenium-catalyzed dehydrogenative silylation step into the reaction sequence is possible. Thus, an orthogonally protected 3-deoxy glycal results via a tandem RCM/hydrosilylation/isomerization sequence. All ruthenium-catalyzed steps of this tandem se-

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Unexpected transfer hydrogenation of C–C-double bonds during Tandem-RCM-isomerization reactions

Cited by 16 publications

References 31 publications

Ru‐ and Pd‐Catalysed Synthesis of 2‐Arylfurans by One‐Flask Heck Arylation/Oxidation

Ru‐ and Pd‐Catalysed Synthesis of 2‐Arylfurans by One‐Flask Heck Arylation/Oxidation

Acyclic Triene Metathesis Polymerization with Chain‐Stoppers: Molecular Weight Control in the Synthesis of Branched Polymers

Synthesis of 3‐Deoxy Glycals via Tandem Metathesis Sequences and Their Use in an Intermolecular Heck Arylation

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