13705-23-2Relevant academic research and scientific papers
Reductive Difunctionalization of Aryl Alkenes with Sodium Metal and Reduction-Resistant Alkoxy-Substituted Electrophiles
Fukazawa, Mizuki,Nogi, Keisuke,Sasamori, Takahiro,Takahashi, Fumiya,Yorimitsu, Hideki
supporting information, (2020/03/13)
A general method for alkali-metal-promoted reductive difunctionalization of alkenes has been developed by means of reduction-resistant alkoxy-substituted electrophiles. A series of 1,2-diboration and 1,2-dicarbofunctionalization products can be synthesize
Heck Reaction of Electronically Diverse Tertiary Alkyl Halides
Kurandina, Daria,Rivas, Mónica,Radzhabov, Maxim,Gevorgyan, Vladimir
supporting information, p. 357 - 360 (2018/01/27)
The efficient Pd-catalyzed Heck reaction of diverse tertiary alkyl halides with alkenes has been developed. Unactivated tertiary alkyl halides efficiently react at room temperature under visible light irradiation with no exogenous photosensitizers required. For activated tertiary alkyl halides, the same catalytic system works well without light. These methods offer a general access to electronically diverse alkenes possessing quaternary and functionalized tertiary allylic carbon centers. The substituents at these centers include alkyl-, carbalkoxy-, tosyl-, phosphonyl-, and boronate groups. It was also shown that the end-game mechanism of this transformation may vary depending on the type of the substrates used.
Platinum(II) olefin hydroarylation catalysts: Tuning selectivity for the anti-Markovnikov product
Clement, Marie L.,Grice, Kyle A.,Luedtke, Avery T.,Kaminsky, Werner,Goldberg, Karen I.
supporting information, p. 17287 - 17291 (2015/02/19)
PtII complexes containing unsymmetrical (pyri-dyl)pyrrolide ligands are shown to catalyze the hydroarylation of unactivated alkenes with selectivity for the anti-Markovnikov product. Substitution on the pyrrolide portion of the ligand allows effective tuning of the selectivity to anti-Markovnikov alkylarene products, whereas substitution on the pyridyl portion can promote competitive al-kenylarene production.
Cu/Ag-catalyzed double decarboxylative cross-coupling reaction between cinnamic acids and aliphatic acids in aqueous solution
Mai, Wen-Peng,Song, Ge,Sun, Gang-Chun,Yang, Liang-Ru,Yuan, Jin-Wei,Xiao, Yong-Mei,Mao, Pu,Qu, Ling-Bo
, p. 19264 - 19267 (2013/10/22)
A novel double decarboxylative cross-coupling catalyzed by copper and silver has been developed. This method provides a practical approach for the flexible synthesis of alkenes and alkynes from the readily affordable substrates.
Copper-catalyzed highly selective semihydrogenation of non-polar carbon-carbon multiple bonds using a silane and an alcohol
Semba, Kazuhiko,Fujihara, Tetsuaki,Xu, Tinghua,Terao, Jun,Tsuji, Yasushi
supporting information; experimental part, p. 1542 - 1550 (2012/08/08)
A copper catalyst bearing a suitable Xantphos derivative or NHC ligand was found to be highly efficient for the selective semihydrogenation of non-polar unsaturated compounds using a mixture of a silane and an alcohol as reducing agent. The catalytic system was useful for the selective semihydrogenation of internal alkynes to (Z)-alkenes with suppression of overreduction to the corresponding alkanes. Furthermore, semihydrogenations of terminal alkyne, 1,2-diene, 1,3-diene, 1,3-enyne and 1,3-diyne systems were also achieved selectively. Copyright
Iron-catalysed, hydride-mediated reductive cross-coupling of vinyl halides and Grignard reagents
Le Bailly, Bryden A. F.,Greenhalgh, Mark D.,Thomas, Stephen P.
supporting information; experimental part, p. 1580 - 1582 (2012/03/26)
An iron-catalysed, hydride-mediated reductive cross-coupling reaction has been developed for the preparation of alkanes. Using a bench-stable iron(ii) pre-catalyst, reductive cross-coupling of vinyl iodides, bromides and chlorides with aryl- and alkyl Grignard reagents successfully gave the products of formal sp3-sp3 cross-coupling reactions.
Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism
Oksdath-Mansilla, Gabriela,Penenory, Alicia B.
, p. 1136 - 1143 (2012/03/10)
The reactions of 2-(4-Z-phenyl)-1,3-dithiane anions (Z=H, OMe, Cl, CN) with neopentyl, neophyl and phenyl iodides were studied in DMSO, taking into consideration the effect of the Z substituent on the dithiane anions reactivity as well as on the product distribution. These substitution reactions proceed by an SRN1 mechanism with radicals and radical anions as intermediates. Two competitive pathways are possible for the radical anion of the substitution product, namely electron transfer (ET) to the substrate giving the substitution product and C-S bond fragmentation to yield a distonic radical anion. ET is the main pathway for the reactions between dithiane anions bearing electron-donor substituents and neopentyl or its analogue iodides affording the substitution products in moderate yields (41-53%). Copyright
Ligandless, anionic, arylpalladium halide intermediates in the heck reaction
Carrow, Brad P.,Hartwig, John F.
supporting information; experimental part, p. 79 - 81 (2010/03/25)
(Chemical Equation Presented) We report the isolation and reactivity of a series of "ligandless," anionic arylpalladium complexes of the general structure [Pd(Ar)Br2]22- by the reaction of (tBu3P)Pd(Ar)(Br) and bromide. These anionic complexes insert olefins at room temperature, and these fast insertions indicate that the anionic complexes are kinetically competent to be intermediates in Heck-Mizoroki reactions conducted under "ligandless" conditions (lacking added dative ligand). Kinetic studies showed that the anionic complexes insert olefins much faster than the corresponding neutral, P(t-Bu)3-ligated complexes. Addition of halide to the reaction of the neutral complex (tBu 3P)Pd(Ar)(Br) and styrene led to a significant rate acceleration, suggesting that the anionic complex forms rapidly and reversibly in situ from the neutral species prior to migratory insertion. These data, along with studies on the regioselectivity for reaction of aryl halides with butyl vinyl ether in the presence of the different starting catalysts, are consistent with the intermediacy of the same anionic, arylpalladium intermediates in Heck reactions catalyzed by palladium complexes containing bulky trialkylphosphine ligands as in reactions conducted under ligandless conditions.
Lithium hydroxide as base in the Wittig reaction. A simple method for olefin synthesis
Antonioletti,Bonadies,Ciammaichella,Viglianti
, p. 4644 - 4648 (2008/09/20)
A mild and practical procedure for the Wittig olefination, promoted by lithium hydroxide and triphenylbenzyl phosphonium bromide, has been set up for the synthesis of stilbenes and styrenes. The experimental conditions allow aromatic, heteroaromatic, unsaturated and saturated aliphatic aldehydes to give final products in good yields.
Strong Bicyclic Guanidine Base-promoted Wittig and Horner-Wadsworth-Emmons Reactions
Simoni, Daniele,Rossi, Marcello,Rondanin, Riccardo,Mazzali, Angelica,Baruchello, Riccardo,Malagutti, Cinzia,Roberti, Marinella,Invidiata, Francesco Paolo
, p. 3765 - 3768 (2007/10/03)
formula presented A convenient procedure to effect the Wittig and Horner-Wadsworth-Emmons reactions employs guanidine TBD and MTBD as base-promoters; mild reaction conditions, high efficiency, and facile isolation of the final products make the present methodology, at least in some cases, a practical alternative to known procedures.
