Nickel(0)-catalyzed cycloaddition of silyl diynes with carbon dioxide to silyl bicyclic .alpha.-pyrones

Tsuda, Toshitaka; Morikawa, Sei; Hasegawa, Naoki; Saegusa, Takeo

doi:10.1021/jo00296a083

Cited by 99 publications

(24 citation statements)

References 4 publications

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“…Some of these nickelacycles are interesting starting products for the syntheses of saturated or unsaturated carboxylic acids or their derivatives, for example by alkylation with alkyl halides [4,5,[18][19][20][21], insertion of unsaturated compounds (CO [10,14,16,20], CO 2 [16,20,22,23], RNC [24,25], alkenes [12,26], alkynes [18,[27][28][29][30][31][32]) or transmetalation reaction with ZnR 2 [33][34][35]. Furthermore, nickelacyclic carboxylates are also found to be useful reagents for the construction of functionalized steroid side chains [36][37][38].…”

Section: Introductionmentioning

confidence: 99%

A new set of nickelacyclic carboxylates (“nickelalactones”) containing pyridine as supporting ligand: synthesis, structures and application in C–C– and C–S– linkage reactions

Langer

Fischer

Görls

et al. 2004

Journal of Organometallic Chemistry

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Section: Introductionmentioning

confidence: 99%

A new set of nickelacyclic carboxylates (“nickelalactones”) containing pyridine as supporting ligand: synthesis, structures and application in C–C– and C–S– linkage reactions

Langer

Fischer

Görls

et al. 2004

Journal of Organometallic Chemistry

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“…Shortly after, the group of Tsuda and Saegusa reported their studies on the Nicatalyzed carboxylative cyclization of 1,6-and 1-7-diynes using phosphine ligands at high pressure CO 2 (50 bar) [123,124]. Unlike the dimerization protocol described by Hoberg, this reaction was proposed to proceed through an initial nickelalactone formation with one of the alkyne terminus followed by carbometalation with the pending alkyne, leading to a seven-membered intermediate that ultimately gives rise to a bicyclic a-pyrone while regenerating the active Ni(0) catalyst.…”

Section: Catalytic Carboxylation Of 13-dienesmentioning

confidence: 99%

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

et al. 2016

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The sustainable utilization of available feedstock materials for preparing valuable compounds holds great promise to revolutionize approaches in organic synthesis. In this regard, the implementation of abundant and inexpensive carbon dioxide (CO2) as a C1 building block has recently attracted considerable attention. Among the different alternatives in CO2 fixation, the preparation of carboxylic acids, relevant motifs in pharmaceuticals and agrochemicals, is particularly appealing, thus providing a rapid and unconventional entry to building blocks that are typically prepared via waste-producing protocols. While significant advances have been realized, the utilization of simple unsaturated hydrocarbons as coupling partners in carboxylation events is undoubtedly of utmost academic and industrial relevance, as two available feedstock materials can be combined in a catalytic fashion. This review article aims to describe the main achievements on the direct carboxylation of unsaturated hydrocarbons with CO2 by using cheap and available Ni or Fe catalytic species.

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“…Scheme 36. Ni-catalyzed butadiene dimerization/carboxylation at high pressure CO 2 [122] Shortly after, the group of Tsuda and Saegusa reported their studies on the Ni-catalyzed carboxylative cyclization of 1,6-and 1-7-diynes using phosphine ligands at high pressure CO 2 (50 bar) [123,124]. Unlike the dimerization protocol described by Hoberg, this reaction was proposed to Ni(cod) proceed through an initial nickelalactone formation with one of the alkyne terminus followed by carbometallation with the pending alkyne, leading to a seven-membered intermediate that ultimately…”

Section: Catalytic Carboxylation Of 13-dienesmentioning

confidence: 99%

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Juliá‐Hernández¹,

Gaydou²,

Serrano³

et al. 2016

Topics in Current Chemistry Collections

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Abstract. The sustainable utilization of available feedstock materials for preparing valuable compounds holds great promise to revolutionize approaches in organic synthesis. In this regard, the implementation of abundant and inexpensive carbon dioxide (CO 2 ) as a C1 building block has recently attracted a considerable attention. Among the different alternatives in CO 2 fixation, the preparation of carboxylic acids, relevant motifs in pharmaceuticals and agrochemicals, is particularly appealing, thus providing a rapid and unconventional entry to building blocks that are typically prepared via wasteproducing protocols. While significant advances have been realized, the utilization of simple unsaturated hydrocarbons as coupling partners in carboxylation events is undoubtedly of utmost academic and industrial relevance, as two available feedstock materials can be combined in a catalytic fashion. This review article aims to describe the main achievements on the direct carboxylation of unsaturated hydrocarbons with CO 2 by using cheap and available Ni or Fe catalytic species.

show abstract

Nickel(0)-catalyzed cycloaddition of silyl diynes with carbon dioxide to silyl bicyclic .alpha.-pyrones

Cited by 99 publications

References 4 publications

A new set of nickelacyclic carboxylates (“nickelalactones”) containing pyridine as supporting ligand: synthesis, structures and application in C–C– and C–S– linkage reactions

A new set of nickelacyclic carboxylates (“nickelalactones”) containing pyridine as supporting ligand: synthesis, structures and application in C–C– and C–S– linkage reactions

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

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