61141-97-7Relevant academic research and scientific papers
Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents
Wang, Gaonan,Gan, Yi,Liu, Yuanhong
supporting information, p. 916 - 920 (2018/09/22)
The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni(cod)2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or arylboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional activators for activation of allylic alcohols.
Stereospecific allyl-aryl coupling catalyzed by in situ generated palladium nanoparticles in water under ambient conditions
Zhao, Jingming,Ye, Jiang,Zhang, Yong Jian
supporting information, p. 491 - 498 (2013/05/09)
A practical process for the stereospecific cross-coupling of secondary allylic carbonates with arylboronic acids has been developed. The reaction is catalyzed by in situ generated palladium nanoparticles (PdNPs) without any ligands and additional stabilizers in water under ambient conditions and furnishes the allyl-aryl coupling products in high isolated yields with high stereospecificities as well as excellent chemo-, regio- and E/Z-selectivities. The in situ generated PdNPs showed extraordinary catalytic activity (S/C up to 5000) even for the allyl-aryl coupling reactions of easily eliminated allylic carbonates under aqueous ambient conditions. The mechanism of the process has also been investigated.
Cross-coupling reactions of allylic alcohols in water
Manabe, Kei,Nakada, Kenji,Aoyama, Naohiro,Kobayashi, Shu
, p. 1499 - 1503 (2007/10/03)
Palladium-catalyzed cross-coupling reactions of allylic alcohols and arylboronic acids in water are described. The reactions proceeded smoothly in water at reflux using catalytic amounts of [Pd(allyl)Cl]2 and PPh3. Addition of a catalytic amount of a base allowed the reaction to proceed even at lower temperatures.
Regio- and enantiospecific rhodium-catalyzed arylation of unsymmetrical fluorinated acyclic allylic carbonates: Inversion of absolute configuration
Evans, P. Andrew,Uraguchi, Daisuke
, p. 7158 - 7159 (2007/10/03)
The transition metal-catalyzed allylic substitution with unstabilized carbon nucleophiles represents an important cross-coupling reaction for the construction of ternary carbon stereogenic centers. We have developed a new regio- and enantiospecific rhodium-catalyzed allylic alkylation of acyclic unsymmetrical chiral nonracemic allylic alcohol derivatives with aryl zinc bromides. This study demonstrates that the hydrotris(pyrazolyl)borate rhodium catalyst and zinc(II) halide salt are crucial for efficiency, while the addition of lithium bromide to the catalyst is necessary for obtaining optimal regiospecificity. The stereochemical course of this reaction was established through the synthesis of (S)-ibuprofen, which demonstrated that the alkylation proceeds with net inversion of absolute configuration consistent with direct addition of the nucleophile to the metal center followed by reductive elimination. Copyright
The Palladium-Catalyzed Cross-Coupling Reaction of Organosilicon Compounds with Allylic Carbonates or Diene Monoxides
Matsuhashi, Hayao,Asai, Satoshi,Hirabayashi, Kazunori,Hatanaka, Yasuo,Mori, Atsunori,Hiyama, Tamejiro
, p. 1943 - 1952 (2007/10/03)
The cross-coupling reaction of allylic carbonates with organosilanes was found to proceed without fluoride ion activation under mild conditions by using a coordinatively unsaturated palladium complex as a catalyst.The reaction was assumed to proceed through an allylpalladium alkoxide derived from the allylic carbonate substrate and a palladium(0) species, the alkoxo ligand activating the organosilicon reagent.Likewise, diene monoxides also underwent cross-coupling with alkenyl- and arylfluorosilanes in moderate to high yields.
Highly reactive forms of zinc and reagents thereof
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, (2008/06/13)
A novel zerovalent zinc species and an organozinc reagent are disclosed. The zerovalent zinc species is directly produced by reaction of a reducing agent on a zinc salt, preferably Zn(CN)2. The organozinc reagent results from the reaction of the zerovalent zinc species and an organic compound having one or more stable anionic leaving groups. These organozinc reagents include a wide spectrum of functional groups in the organic radical, and are useful in a variety of reactions schemes.
The Direct Formation of Functionalized Alkyl(aryl)zinc Halides by Oxidative Addition of Highly Reactive Zinc with Organic Halides and Their Reactions with Acid Chlorides, α,β-Unsaturated Ketones, and Allylic, Aryl, and Vinyl Halides
Zhu, Lishan,Wehmeyer, Richard M.,Rieke, Reuben D.
, p. 1445 - 1453 (2007/10/02)
Highly reactive zinc, prepared by the lithium naphthalenide reduction of ZnCl2, readily undergoes oxidative addition to alkyl, aryl, and vinyl halides under mild conditions to generate the corresponding organozinc compounds in excellent yields.Significantly, the reaction will tolerate a spectrum of functional groups on the organic halides.Accordingly, this approach can now be used to prepare a wide variety of highly functionalized organozinc compounds.In the presence of Cu(I) salts, the organozinc compounds cross-couple with acid chlorides, conjugatively add to α,β-unsaturated ketones, and regioselectively undergo SN2' substitution reactions with allylic halides.They also cross-couple with aryl or vinyl halides with Pd(0) catalysts.
