Titanium‐Catalyzed Exhaustive Reduction of Oxo‐Chemicals DOI
Bo Han,

Chunping Ren,

Min Jiang

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 134(46)

Published: Sept. 20, 2022

Abstract Catalytic reduction of carboxylic acids and derivatives all the way to their corresponding methyl‐compounds is very rare still challenging for homogeneous transition‐metal catalysis. Herein, we report an unprecedented general catalytic exhaustive functional group straightforwardly a methyl group. This reaction was achieved using earth‐abundant readily available titanium as catalyst. Our system has broad tolerance works various other types oxo‐chemicals such alcohols, aldehydes, ketones, lactones, carboxylates (>100 examples). Preliminary mechanistic studies revealed that in situ‐generated Ti III −H species vital this transformation.

Language: Английский

The Direct Mechanocatalytic Suzuki–Miyaura Reaction of Small Organic Molecules DOI
Wilm Pickhardt,

Claudio Beaković,

Maike Mayer

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(34)

Published: May 31, 2022

Abstract The molecular Suzuki cross‐coupling reaction was conducted mechanochemically, without solvents, ligands, or catalyst powders. Utilizing one catalytically active palladium milling ball, products could be formed in quantitative yield as little 30 min. In contrast to previous reports, the adjustment of parameters led complete elimination abrasion from thus enabling first reported systematic analysis. XPS, situ XRD, and reference experiments provided evidence that ball surface location catalysis, allowing a mechanism proposed. versatility approach demonstrated by extending substrate scope deactivated even sterically hindered aryl iodides bromides.

Language: Английский

Citations

39
Mechanochemical Divergent Syntheses of Oxindoles and α‐Arylacylamides via Controllable Construction of C−C and C−N Bonds by Copper and Piezoelectric Materials DOI

Honggui Lv,

Xinyue Xu, Jing Li

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(34)

Published: June 29, 2022

Abstract Herein, we present the divergent syntheses of α‐arylacylamides and oxindoles via mechanoredox chemistry by using easily accessible α‐bromo N ‐sulfonyl amides as starting materials. Our system consists a catalytic amount Cu II precatalyst piezoelectric The highly polarized BaTiO 3 or PbTiO under mechanical agitation can act an electron donor to realize recycling I . Control experiments density functional theory calculations have been performed support proposed mechanistic rationale for cascade reactions.

Language: Английский

Citations

28
Titanium‐Catalyzed Exhaustive Reduction of Oxo‐Chemicals DOI
Bo Han,

Chunping Ren,

Min Jiang

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(46)

Published: Sept. 20, 2022

Catalytic reduction of carboxylic acids and derivatives all the way to their corresponding methyl-compounds is very rare still challenging for homogeneous transition-metal catalysis. Herein, we report an unprecedented general catalytic exhaustive functional group straightforwardly a methyl group. This reaction was achieved using earth-abundant readily available titanium as catalyst. Our system has broad tolerance works various other types oxo-chemicals such alcohols, aldehydes, ketones, lactones, carboxylates (>100 examples). Preliminary mechanistic studies revealed that in situ-generated TiIII -H species vital this transformation.

Language: Английский

Citations

22
Piezoelectric Metal‐Organic Frameworks Mediated Mechanoredox Borylation and Arylation Reactions by Ball Milling DOI

Run-Dong Ding,

Qing Liu, Lifei Zheng

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(20)

Published: Jan. 9, 2023

Herein, metal-organic frameworks UiO-66 and UiO-66-NH2 were synthesized, their piezoelectric properties characterized by piezoresponse force microscopy. Under mechanical agitation, the highly polarized can act as electron donors to reduce aryl diazonium salts, forming radical species, which further react with bis(pinacolato)diborane or heteroarenes generate desired products broad substrate scope. For all substrates, it was found that reactions mediated , exhibited better property, more efficient than those promoted UiO-66. Moreover, shown convenient regeneration of spent catalysts be reused for promoting mechanoredox without loss activities taking advantage unmatched repairability frameworks. Mechanistic studies revealed a pathway involved in these transformations.

Language: Английский

Citations

12
Die direkte mechanokatalytische Suzuki–Miyaura‐Kupplung kleiner organischer Moleküle DOI
Wilm Pickhardt,

Claudio Beaković,

Maike Mayer

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 134(34)

Published: May 31, 2022

Abstract In dieser Arbeit wird die Suzuki–Miyaura‐Reaktion in Abwesenheit von Lösungsmitteln, Liganden und pulverförmiger Katalysatoren vorgestellt. Unter Verwendung einer einzelnen katalytisch aktiven Mahlkugel können quantitative Ausbeuten nach 30 min des Vermahlens isoliert werden. Weiterhin führten Anpassungen der Mahlparameter dazu, dass Materialverlust durch Kugelabrieb vermieden wurde. Anhand dieses abriebfreien Systems Röntgenphotoelektronenspektroskopie, situ Röntgendiffraktrometrie, sowie Referenzexperimente bewiesen, katalytische Reaktion auf Kugeloberfläche stattfindet. Die Vielseitigkeit neuartigen Katalysekonzepts anhand verschiedener Edukte verdeutlicht. Aktivierte, deaktivierte, sterisch‐gehinderte Aryliodide ‐bromide werden innerhalb kurzer Zeit guten gekuppelt.

Citations

6
Mechanochemical Divergent Syntheses of Oxindoles and α‐Arylacylamides via Controllable Construction of C−C and C−N Bonds by Copper and Piezoelectric Materials DOI

Honggui Lv,

Xinyue Xu, Jing Li

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 134(34)

Published: June 29, 2022

Abstract Herein, we present the divergent syntheses of α‐arylacylamides and oxindoles via mechanoredox chemistry by using easily accessible α‐bromo N ‐sulfonyl amides as starting materials. Our system consists a catalytic amount Cu II precatalyst piezoelectric The highly polarized BaTiO 3 or PbTiO under mechanical agitation can act an electron donor to realize recycling I . Control experiments density functional theory calculations have been performed support proposed mechanistic rationale for cascade reactions.

Language: Английский

Citations

4
Titanium‐Catalyzed Exhaustive Reduction of Oxo‐Chemicals DOI
Bo Han,

Chunping Ren,

Min Jiang

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 134(46)

Published: Sept. 20, 2022

Abstract Catalytic reduction of carboxylic acids and derivatives all the way to their corresponding methyl‐compounds is very rare still challenging for homogeneous transition‐metal catalysis. Herein, we report an unprecedented general catalytic exhaustive functional group straightforwardly a methyl group. This reaction was achieved using earth‐abundant readily available titanium as catalyst. Our system has broad tolerance works various other types oxo‐chemicals such alcohols, aldehydes, ketones, lactones, carboxylates (>100 examples). Preliminary mechanistic studies revealed that in situ‐generated Ti III −H species vital this transformation.

Language: Английский

Citations

0