Utilization of Synthetic Calcium‐Phyllosilicates as Bifunctional Bases in the Matsuda‐Heck Reaction

Brunner, Heiko; Vedder, L.

doi:10.1002/cctc.201801519

Cited by 8 publications

(15 citation statements)

References 40 publications

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“…Compared to the prior results published by Correia and Pastre (Entry 6, Table ) the presented synthetic protocol utilizing an in situ generated palladium on aluminum oxide distinguishes itself by a higher yield and more benign reaction conditions.…”

Section: Resultsmentioning

confidence: 67%

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Benign Arylations of Dimethyl Itaconate via Heck–Matsuda Reaction Utilizing in‐Situ Generated Palladium on Aluminum Oxide

et al. 2020

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Section: Resultsmentioning

confidence: 67%

“…The Heck–Matsuda reaction, which has provided valuable services in organic synthesis over the past decades, opens up a way out of the limitations of the previous presentation methods described above …”

Section: Introductionmentioning

confidence: 99%

Benign Arylations of Dimethyl Itaconate via Heck–Matsuda Reaction Utilizing in‐Situ Generated Palladium on Aluminum Oxide

et al. 2020

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“…The expected product 7ca was isolated in a low yield of 28%, whereas the double arylated product 9ca was obtained in a somewhat higher yield of 41%, even though only 1.2 equiv of diazonium salt was used. Although geminal Matsuda-Heck diarylations have occasionally been reported as side reactions, , examples for the intentional double arylation are scarce and normally require special conditions or catalysts , or at least a 2-fold excess of diazonium salt . Currently, it remains unclear why the double arylated compound 9ca is the major product in this case.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Arylidene-β-lactams via exo-Selective Matsuda-Heck Arylation of Methylene-β-lactams

Riemer

Krüger

et al. 2021

J. Org. Chem.

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exo-Methylene-β-lactams were synthesized in two steps from commercially available 3-bromo-2-(bromomethyl)propionic acid and reacted with arene diazonium salts in a Heck-type arylation in the presence of catalytic amounts of Pd(OAc) 2 under ligand-free conditions. The products, arylidene-βlactams, were obtained in high yields as single isomers. The βhydride elimination step of the Pd-catalyzed coupling reaction proceeds with high exo-regioselectivity and E-stereoselectivity. With aryl iodides, triflates, or bromides, the coupling products were isolated only in low yields, due to extensive decomposition of the starting material at elevated temperatures. This underlines that arene diazonium salts can be superior arylating reagents in Hecktype reactions and yield coupling products in synthetically useful yields and selectivities when conventional conditions fail.

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“…Most importantly, they are also the Pd catalyst for cross-coupling. Additionally, synthetic calcium-phyllosilicates can also serve as bifunctional bases in the Matsuda–Heck reaction using methanol as the solvent . This heterogeneous catalytic protocol provides a complementary route to synthesize acid-sensitive products.…”

Section: Aryl C–c Bond Formationsmentioning

confidence: 99%

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

et al. 2021

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Aryl diazonium salts are versatile building blocks in organic synthesis. In light of the ever-increasing importance of aryl diazonium salts spanning most disciplines of the chemical sciences, we review the recent development of aryl diazonium chemistry over the past seven years (2013−2020). Special emphasis is put on various new transformations involving the generation of radical intermediates via thermal, photochemical, and electrochemical means. Recent advances in the development of transition metal-catalyzed reactions using aryl diazonium salts are also reviewed. Together, these newly developed transformations significantly expand the synthetic chemist's repertoire of aromatic carbon−carbon and carbon−heteroatom bond forming methods using aryl diazonium precursors, providing powerful tools for the synthesis and modification of complex molecular scaffolds.

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Utilization of Synthetic Calcium‐Phyllosilicates as Bifunctional Bases in the Matsuda‐Heck Reaction

Abstract: Calcium‐phyllosilicates can successfully be used as novel bases in the Matsuda‐Heck reaction using methanol as solvent. The new experimental set‐up distinguishes itself by higher reactivity and better selectivity compared to other systems.

Cited by 8 publications

References 40 publications

Benign Arylations of Dimethyl Itaconate via Heck–Matsuda Reaction Utilizing in‐Situ Generated Palladium on Aluminum Oxide

Benign Arylations of Dimethyl Itaconate via Heck–Matsuda Reaction Utilizing in‐Situ Generated Palladium on Aluminum Oxide

Synthesis of Arylidene-β-lactams via exo-Selective Matsuda-Heck Arylation of Methylene-β-lactams

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

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