Arenediazonium o-benzenedisulfonimides as efficient reagents for Heck-type arylation reactions

Artuso, Emma; Barbero, Margherita; Degani, Iacopo; Dughera, Stefano; Fochi, Rita

doi:10.1016/j.tet.2006.01.027

Cited by 50 publications

(22 citation statements)

References 44 publications

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“…Although yields were generally high when using other arenediazonium tetrafluoroborates, reaction times (12 h) are considerably longer than those required when using the homogeneous catalyst Pd-(OAc) 2 . [24,25] In the same report, recycling studies for a heterogeneous catalyst were reported for the first time since Beller's earlier publication (Table 3, Entries 11 and 12). Upon first re-use, 2-methylbenzenediazonium tetrafluoroborate was coupled to methyl acrylate in moderate yield, and deactivation of the catalyst was rationalized by an apparent leaching of Pd into the solution as evidenced by the change in crystallite size of the nanoparticles from 20 to 60 nm.…”

Section: Heterogeneous Catalysismentioning

confidence: 97%

Evolution and Synthetic Applications of the Heck–Matsuda Reaction: The Return of Arenediazonium Salts to Prominence

2011

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This review highlights the potential and the versatility of arenediazonium salts as viable alternatives to conventional aryl halides and oxygen-based electrophiles for Pd-catalyzed Heck reactions. It also presents an overview of the field over the last decade, including some historical perspective of the Heck-Matsuda (HM) reaction with general considerations regarding reaction conditions, type of catalysts used, and the application of arenediazonium salts as reagents for the HM arylation of several types of alkenes. Throughout this review, the principal aspects related to reactivity and selectivity are discussed, and when applicable a comparison is made between the HM and the conventional Heck reactions. Onepot procedures that involve generation of the arenediazonium salt in situ from the corresponding aniline have been

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Section: Heterogeneous Catalysismentioning

confidence: 97%

Evolution and Synthetic Applications of the Heck–Matsuda Reaction: The Return of Arenediazonium Salts to Prominence

2011

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“…Some common olefinic substrates used in this reaction were arylated by a wide range of arenediazonium salts 67 in the presence of Pd(OAc) 2 (1 mol% with respect to 67), in a suitable organic solvent. No ligands were necessary, complete stereoselectivity was observed and yields were excellent, regardless of the nature of the substituents (this finding being in contrast with the difficulties reported in literature for nitro substituted arenediazonium tetrafluoroborates [52] Dry arenediazonium o-benzenedisulfonimides were used in palladium-catalyzed arylation of allylic alcohols [53]. As known from literature, such reactions are generally poorly regiospecific and lead to mixtures of β-and α-arylated both carbonyl compounds and allylic alcohols; selective procedures have been proposed, but only a few reports refer to arylation by arenediazonium salts.…”

Section: Heck-type Arylation Reactionsmentioning

confidence: 58%

o-Benzenedisulfonimide: An Organic Reagent and Organocatalyst of Renewed Interest

Barbero¹,

Bazzi

Cadamuro

et al. 2011

COC

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ABSTRACT:Synthesized nearly one century ago as a saccharine-like sweetener compound, the obenzenedisulfonimide has received a discontinuous attention in the past. In the last century, various synthetic procedures have been reported, in confirmation of the interest in this intriguing compound. In recent years, it has been used as a leaving group in reactions of nucleophilic substitution of amines with alcohols or phenols to give the corresponding ethers. Its Nfluoroderivative is a stable and efficient fluorinating agent, which has found applications in several asymmetric syntheses. In previous studies, its conjugated base has been extensively used as stabilizing counter-ion of arenediazonium salts; safely isolated and stored in a dry state, ready to use, they have been applied successfully in many dediazoniation reactions, with interesting mechanistic insights. More recently, due to its high acidity, the o-benzenedisulfonimide has been used in catalytic amounts in some common acid-catalyzed organic reactions. Valuable aspects of this catalyst are its easy recovery from the reaction mixture and its reuse in other reactions, with clear economic and ecological advantages. Finally, the disulfonimide functional group has been proposed as a powerful chiral motif for strong Brønsted acids in asymmetric organocatalysis.

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“…The conversions were 100% except for entry 8 which had a conversion of 90%. Table 4 shows the results obtained from the Heck-type reactions using arenediazonium o-benzenedisulfonimides 1 [48], tetrafluoroborates 2 [20,49,50], and the reported aryldiazonium silica sulfates 3. The comparison of theses data confirms that the presented study has provided a relatively rapid manner to perform Heck-type reactions in high yields.…”

Section: Heck-type Arylation Of Aryldiazonium Silica Sulfatesmentioning

confidence: 99%

Heck-type reaction of aryldiazonium silica sulfates

et al. 2011

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Aryldiazonium silica sulfates were employed as new and efficient reagents for Heck-type arylation reactions with styrene and methyl acrylate. The reactions were carried out in an organic solvent, in the presence of Pd(OAc) 2 as precatalyst without use of base and free ligand. The trans isomers of desired products, methyl cinnamates and stilbenes, were obtained with full conversion. Use of a catalytic amount of Pd(OAc) 2 produced the corresponding products in short reaction times and excellent yields.

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Arenediazonium o-benzenedisulfonimides as efficient reagents for Heck-type arylation reactions

Cited by 50 publications

References 44 publications

Evolution and Synthetic Applications of the Heck–Matsuda Reaction: The Return of Arenediazonium Salts to Prominence

Evolution and Synthetic Applications of the Heck–Matsuda Reaction: The Return of Arenediazonium Salts to Prominence

o-Benzenedisulfonimide: An Organic Reagent and Organocatalyst of Renewed Interest

Heck-type reaction of aryldiazonium silica sulfates

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