ChemInform Abstract: Palladium‐Catalyzed Cross‐Coupling Alkylation of Arenediazonium o‐Benzenedisulfonimides.

Barbero, Margherita; Cadamuro, Silvano; Dughera, Stefano

doi:10.1002/chin.200822062

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In contrast to numerous examples of cross-coupling reactions between arenediazonium salts and aromatic or alkenyl organometallic compounds, very few examples are reported with alkyl organometallic compounds. Salts 67 were successfully tested in such palladium-catalyzed alkylation [56]. By reaction with tetramethyl or tetrabutyltin 120 (1.1 equiv), in THF at room temperature or in acetonitrile at 40 °C, in the presence of Pd(OAc) 2 2.5 mol%, chemoselective methylation and butylation products 121 and 122 were obtained in high and modest yields, respectively; the presence of arenes 123, formed by hydrodediazoniation, was nearly always observed and often made purifications difficult (Scheme 40).…”

Section: Palladium-catalyzed Cross-coupling Reactions With Aryl and Amentioning

confidence: 99%

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

Barbero¹,

Bazzi

Cadamuro

et al. 2011

COC

View full text Add to dashboard Cite

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.

show abstract

Section: Palladium-catalyzed Cross-coupling Reactions With Aryl and Amentioning

confidence: 99%

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

Barbero¹,

Bazzi

Cadamuro

et al. 2011

COC

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: Palladium‐Catalyzed Cross‐Coupling Alkylation of Arenediazonium o‐Benzenedisulfonimides.

Cited by 1 publication

References 1 publication

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

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

Contact Info

Product

Resources

About