Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes
نویسندگان
چکیده
The cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate (2) with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3 afforded the mono-coupled products 3 and 5 in high yields. The use of 4 equiv of boronic acids in the presence of catalytic amount of Pd(PPh3)2Cl2 and Na2CO3 in this reaction resulted in the formation of symmetrical di-coupled products 4 in high yields. Unsymmetrical di-coupled products 4 were obtained in high yields from the reactions of 3 with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3.
منابع مشابه
Efficient synthesis of silylated 2,2-difluorostyrene derivatives through Suzuki-Miyaura cross-coupling of 2,2-difluoro-1-iodo-1-silylethenes.
We report a new synthetic sequence for the preparation of silylated 2,2-difluorostyrene derivatives. This new route has numerous advantages over the previous one including enhanced scope, higher yields, ease of purification, and significant reduction of the amount of desilylated side-products. An unexpected transformation of a silylated 2,2-difluorostyrene derivative is also presented.
متن کاملArylation of rhodium(II) azavinyl carbenes with boronic acids.
A highly efficient and stereoselective arylation of in situ-generated azavinyl carbenes affording 2,2-diaryl enamines at ambient temperatures has been developed. These transition-metal carbenes are directly produced from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of a rhodium carboxylate catalyst. In several cases, the enamines generated in this reaction can be cycl...
متن کاملPalladium-Catalyzed Defluorinative Coupling of 1-Aryl-2,2-Difluoroalkenes and Boronic Acids: Stereoselective Synthesis of Monofluorostilbenes.
The palladium-catalyzed defluorinative coupling of 1-aryl-2,2-difluoroalkenes with boronic acids is described. Broad functional-group tolerance arises from a redox-neutral process by a palladium(II) active species which is proposed to undergo a β-fluoride elimination to afford the products. The monofluorostilbene products were formed with excellent diastereoselectivity (≥50:1) in all cases, and...
متن کاملA new approach for the synthesis of 3,4-dihydropyrano[c]chromenes and biscoumarins using {[2,2’-BPyH][C(CN)3]2} as a bifunctional nanostructured ionic liquid catalyst
[2,2'-Bipyridine]-1,1'-diium tricyanomethanide {[2,2'-BPyH][C(CN)3]2} as a bifunctional nanostructured ionic liquid catalyst (0.5 mol%) was used for the synthesis of 3,4-dihydropyrano[c]chromenes (14 examples) under solvent-free condition at room temperature in high yield (82-91%) and short reaction time. In addition, the described ionic liquid catalyst was also applied for the synthesis of bis...
متن کاملCopper(i)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling.
Using a simple copper(i) catalyst has allowed a high yielding sulfonylative-Suzuki-Miyaura cross-coupling reaction to be developed. The process provides a single step route to diaryl sulfones from the direct combination of aryl boronic acids, sulfur dioxide and aryl iodides, and represents the first sulfonylative variant of a classic cross-coupling reaction. Sulfur dioxide is delivered from the...
متن کامل