2004
DOI: 10.1016/j.jorganchem.2003.11.025
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Tetraphenylantimony carboxylates in the cascade Pd-catalyzed C-phenylation reaction of methyl acrylate in the presence of peroxide

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Cited by 30 publications
(7 citation statements)
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“…[21] These cross-coupling reactions of arylantimony compounds with arylboronic acids or alkynes smoothly proceed in the absence of base reagents and copper cocatalysts. Pentavalent organoantimony(V) compounds could be also used as psedo-arylhalides for Pdcatalyzed CÀ C(Ar) bond formation in Heck-, [22][23][24] Stille-, [25] and Hiyama-type reactions. [26] Based on these knowledges, we initially focused on achieving the Pd catalyzed CÀ H arylation of benzothiophene (1 a) using organoantimony or bismuth compounds 2 a-9 ( Table 1).…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…[21] These cross-coupling reactions of arylantimony compounds with arylboronic acids or alkynes smoothly proceed in the absence of base reagents and copper cocatalysts. Pentavalent organoantimony(V) compounds could be also used as psedo-arylhalides for Pdcatalyzed CÀ C(Ar) bond formation in Heck-, [22][23][24] Stille-, [25] and Hiyama-type reactions. [26] Based on these knowledges, we initially focused on achieving the Pd catalyzed CÀ H arylation of benzothiophene (1 a) using organoantimony or bismuth compounds 2 a-9 ( Table 1).…”
Section: Resultsmentioning
confidence: 99%
“…2,5-Dimethylthiophene also afforded βphenylated product (23) in moderate yield. Furthermore, 3substituted thiophenes were treated with 2 a to give the corresponding products (24)(25)(26) in satisfactory yields. The reaction of 2 a with 2-and 3-acetylthiophenes, and 2-iodothiophene, and thiophene gave a complex mixture under these conditions (data not shown).…”
Section: Resultsmentioning
confidence: 99%
“…Triarylantimony dicarboxylates act as effective arylating agents in Pd-catalyzed C-C(Ar) bond formation reactions such as [28][29][30] 31) and Hiyama-type 32) reactions. Over the past few years, we have also found that they are an efficient aryl donors in base-free Suzuki-type reactions and copper-and base-free Sonogashira-type reactions.…”
Section: The Reaction Of Triarylantimony Diacetates [Ar 3 Sb(oac) 2 ]mentioning
confidence: 99%
“…Therefore, the development of an effective novel aryl donor and the elucidation of its reactivity for the C–H arylation of benzofuran derivatives are required. Pentavalent organoantimony compounds such as triarylantimony diacetates [Ar 3 Sb(OAc) 2 ] and tetraphenylantimony acetate [Ph 4 Sb(OAc)] could be used as pseudo-halides for Pd-catalyzed C–C(Ar) bond formation in Heck- [ 30 , 31 , 32 ], Stille- [ 33 ], Hiyama- [ 34 ], Suzuki- [ 35 , 36 ] and Sonogashira-type reactions [ 37 ]. We also recently reported that triarylantimony difluorides (Ar 3 SbF 2 ) serve as an arylating reagent for the Pd-catalyzed β-selective C–H arylation of thiophenes [ 38 ].…”
Section: Introductionmentioning
confidence: 99%