Recent advances in the Heck–Matsuda reaction in heterocyclic chemistry

Felpin, François‐Xavier; Nassar‐Hardy, Luma; Callonnec, François Le; Fouquet, Éric

doi:10.1016/j.tet.2011.02.051

Cited by 232 publications

(91 citation statements)

References 134 publications

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“…[30][31][32][33][34] Diazonium salts have first been used in Pd-catalyzed coupling reactions more than thirty years ago [35] and their synthetic utility has recently been described in excellent reviews. [36][37][38] Nevertheless, they are still not fully recognized as valuable alternatives to aryl iodides or triflates. In particular, coupling reactions of arene diazonium salts and alkynes have not yet been developed to the same maturity as alkyne/aryl halide couplings.…”

Section: Introductionmentioning

confidence: 99%

Pd‐Catalyzed [2+2+1] Coupling of Alkynes and Arenes: Phenol Diazonium Salts as Mechanistic Trapdoors

Schmidt¹,

Berger²,

Kelling³

et al. 2011

Chemistry A European J

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Section: Introductionmentioning

confidence: 99%

Pd‐Catalyzed [2+2+1] Coupling of Alkynes and Arenes: Phenol Diazonium Salts as Mechanistic Trapdoors

Schmidt¹,

Berger²,

Kelling³

et al. 2011

Chemistry A European J

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“…Accordingly, the diallyl ethers 11, conveniently available with a variety of R substituents, were envisaged as starting materials. Subjection of these diallyl ethers to an RCM/ isomerization sequence [19][20][21][22] should yield the 2-substituted 2,3-dihydrofurans 12, which should react with the arenediazonium salts 13 under Pd-catalysis conditions [23][24][25] to afford the 2,5-disubstituted 2,5-dihydrofurans 14. [18] Oxidation or dehydrogenation of these intermediates should give the desired 2,5-disubstituted furans 15.…”

Section: Introductionmentioning

confidence: 99%

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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“…The Mizoroki-Heck reactions have exhibited good functional group tolerance with a wide range of substrates under mild conditions. At present, not only aryl, vinyl, benzyl, and alkyl halides [1][2][3][4][5][6], but also the corresponding pseudo halides such as sulfonates [10][11][12], sulfonyl chlorides [13][14][15], carboxylic acid derivatives [16][17][18], diazonium salts [19][20][21], iodonium salts [22,23], phosphonium salts [24], and sulfonium salts [25], have been successfully employed as electrophiles in Heck-type cross-couplings. Both electron-poor and -rich alkenes (such as acrylic esters, enolethers, and ethylene) have proved to be viable cross-coupling partners in the reactions [1][2][3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Pd-Catalyzed Mizoroki-Heck Reactions Using Fluorine-Containing Agents as the Cross-Coupling Partners

Yang

Zhao

et al. 2018

Catalysts

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Abstract:The Mizoroki-Heck reaction represents one of the most convenient methods for carbon-carbon double bond formation in the synthesis of small organic molecules, natural products, pharmaceuticals, agrochemicals, and functional materials. Fluorine-containing organic compounds have found wide applications in the research areas of materials and life sciences over the past several decades. The incorporation of fluorine-containing segments into the target molecules by the Mizoroki-Heck reactions is highly attractive, as these reactions efficiently construct carbon-carbon double bonds bearing fluorinated functional groups by simple procedures. This review summarizes the palladium-catalyzed Mizoroki-Heck reactions using various fluorine-containing reagents as the cross-coupling partners. The first part of the review describes the Pd-catalyzed Mizoroki-Heck reactions of aryl halides or pseudo-halides with the fluorinated alkenes, and the second part discusses the Pd-catalyzed Mizoroki-Heck reactions of the fluorinated halides or pseudo-halides with alkenes. Variants of the Pd-catalyzed Mizoroki-Heck reactions with fluorine-containing reagents are also briefly depicted. This work supplies an overview, as well as a guide, to both younger and more established researchers in order to attract more attention and contributions in the realm of Mizoroki-Heck reactions with fluorine-containing participants.

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Recent advances in the Heck–Matsuda reaction in heterocyclic chemistry

Cited by 232 publications

References 134 publications

Pd‐Catalyzed [2+2+1] Coupling of Alkynes and Arenes: Phenol Diazonium Salts as Mechanistic Trapdoors

Pd‐Catalyzed [2+2+1] Coupling of Alkynes and Arenes: Phenol Diazonium Salts as Mechanistic Trapdoors

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

Pd-Catalyzed Mizoroki-Heck Reactions Using Fluorine-Containing Agents as the Cross-Coupling Partners

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