140-67-0Relevant articles and documents
Regioselective Allylmetalation of Allenes with Tetraallylmanganate or Allylmagnesium Chloride under MnCl2 Catalysis
Nishikawa, Toshihiro,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 4623 - 4626 (2003)
(Equation presented) Treatment of allenes with tetraallylmanganate provides allylated products with high regioselectivity. A catalytic amount of MnCl2 combined with allylmagnesium chloride also achieves efficient allylmetalatlon of allenes. The resulting alkenylmagnesium spedes react with various electrophiles. In the presence of molecular oxygen, the alkenylmagnesium undergoes diallylation reaction. A cyclization reaction of 1,2,6-heptatriene with tetraallylmanganate is also described.
Stannylated polynorbornenes as new reagents for a clean stille reaction
Carrera, Nora,Gutierrez, Enrique,Benavente, Rut,Villavieja, M. Mar,Albeniz, Ana C.,Espinet, Pablo
, p. 10141 - 10148 (2008)
New functionalized polynorbornenes have been obtained in good yields by vinylic copolymerization of norbornene with a (norbornenyl)Sn-Bu2Cl monomer, catalyzed by [Ni(C6F5)2(SbPh 3)2]. Subsequent functionalization produces a wide variety of polymers with different -SnBu2R groups (R = aryl, vinyl, alkynyl). The polymers can be used as R-transfer reagents in Stille couplings, thereby providing easy workup and separation of the polymeric tin byproducts from the coupling products. Tin contents of around 0.05 wt% are found in the Stille products. The stannylated polymers can be recycled and reused with good efficiency.
A novel palladium catalyst for cross-coupling of allyl acetates with arylboronic acids
Bouyssi, Didier,Gerusz, Vincent,Balme, Genevieve
, p. 2445 - 2448 (2002)
The palladium-catalyzed coupling reactions of various arylboronic acids and allylic acetates take place readily under mild conditions. The choice of ligand in the palladium catalyst and the solvent are critical to the yields of coupled products. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Electron-transfer-induced intermolecular [2 + 2] cycloaddition reactions based on the aromatic "redox tag" strategy
Okada, Yohei,Nishimoto, Asaki,Akaba, Ryoichi,Chiba, Kazuhiro
, p. 3470 - 3476 (2011)
Novel electron-transfer-induced intermolecular [2 + 2] cycloaddition reactions between an aliphatic cyclic enol ether and several unactivated olefins have been demonstrated on the basis of the aromatic "redox tag" strategy. The aromatic "redox tag" was oxidized during the formation of the cyclobutane ring, affording the relatively long-lived aromatic radical cation, which was then reduced to complete the overall reaction that constructed the corresponding [2 + 2] cycloadducts. The aromatic "redox tag" was also found to facilitate electron-transfer-induced cycloreversion reactions of cyclobutane rings.
Nickel-Catalyzed Negishi-Type Arylation of Trialkylsulfonium Salts
Minami, Hiroko,Nogi, Keisuke,Yorimitsu, Hideki
supporting information, p. 1542 - 1546 (2021/09/06)
Negishi-type arylation of trialkylsulfonium salts with arylzinc reagents has been accomplished under nickel catalysis. The use of cyclohexanethiol as an additional ligand was found to be particularly important to promote C-S cleavage. The present reaction accommodates one-pot arylation of dialkyl sulfides by combining with S -methylation with MeOTf. Mechanistic experiments suggest that C-S cleavage would proceed via single-electron transfer (SET) to generate the most stable carbon-centered radical and that the thiolate ligand would promote the C-S cleavage and radical recombination step.
Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold
Fiorio, Jhonatan L.,Rossi, Liane M.
, p. 312 - 318 (2021/01/29)
The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is
Manganese catalyzed dehydrogenative silylation of alkenes: Direct access to allylsilanes
Wu, Shang,Zhang, Ying,Jiang, Hongyan,Ding, Ning,Wang, Yanbin,Su, Qiong,Zhang, Hong,Wu, Lan,Yang, Quanlu
supporting information, (2020/06/03)
Dehydrogenative silylation of alkenes with silanes to produce allylsilanes is achieved through manganese catalysis with a wide scope of substrate tolerance. This transformation involves silane radicals initiated by manganese complex without additional oxidant additives. It offers a general, convenient and practical protocol with excellent functional group compatibility and gram-scale capacity for the modular synthesis of allylsilanes.