26057-47-6Relevant academic research and scientific papers
Stereoselective synthesis of 1,4-dienes by chelation-controlled reduction of benzothiazole β-oxosulfides
Calo, Vincenzo,Nacci, Angelo
, p. 3825 - 3828 (1998)
Allylated β-oxosulfides of benzothiazole can replace β-oxophosphane oxides to provide a stereospecific alkene synthesis. These sulfides, by reduction with sodium borohydride afford predominantly syn β-hydroxy sulfides. DIBAL reduction in the presence of magnesium bromide improves the syn stereomer formation. Base treatment of these β-hydroxy sulfides affords (Z)-allyl thiiranes which are converted into (E, Z)-dienes.
Microwave-enhanced palladium-catalyzed cross-coupling reactions of potassium vinyltrifluoroborates and allyl acetates: A new route to 1,4-pentadienes
Kabalka, George W.,Al-Masum, Mohammad
, p. 11 - 13 (2006)
(Chemical Equation Presented) A novel and straightforward microwave synthesis of 1,4-pentadienes has been developed involving the cross-coupling of potassium vinyltrifluoroborates and allyl acetates in the presence of a palladium catalyst.
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.
Dehydrative cross-coupling reactions of allylic alcohols with olefins
Gumrukcu, Yasemin,De Bruin, Bas,Reek, Joost N. H.
supporting information, p. 10905 - 10909 (2014/09/17)
The direct dehydrative activation of allylic alcohols and subsequent cross-coupling with alkenes by using palladium catalyst containing a phosphoramidite ligand is described. The activation of the allyl alcohol does not require stoichiometric additives, thus allowing clean, waste-free reactions. The scope is demonstrated by application of the protocol to a series allylic alcohols and vinyl arenes, leading to variety of 1,4-diene products. Based on kinetic studies, a mechanism is proposed that involves a palladium hydride species that activates the allyl alcohol to form the allyl intermediate.
Iridium-catalyzed enantioselective allylic vinylation
Hamilton, James Y.,Sarlah, David,Carreira, Erick M.
supporting information, p. 994 - 997 (2013/04/10)
The first example of Ir-catalyzed asymmetric substitution reaction with vinyl trifluoroborates is described. The direct reaction between branched, racemic allylic alcohols and potassium alkenyltrifluoroborates proceeded with high site selectivity and exce
Regioselective and stereospecific cross-coupling of primary allylic amines with boronic acids and boronates through palladium-catalyzed C-N bond cleavage
Li, Man-Bo,Wang, Yong,Tian, Shi-Kai
supporting information; experimental part, p. 2968 - 2971 (2012/04/18)
The NH2 group serves as an effective leaving group in the palladium-catalyzed regioselective and stereospecific title reaction (see scheme). The reaction works well with aryl- and alkenylboronic acids and aryl-, alkenyl-, allyl-, and benzylboronates, and complete transfer of chirality has been achieved when using α-chiral primary allylic amines as the allylic electrophiles. Copyright
Palladium-catalyzed cross-coupling reactions of organogold(i) phosphanes with allylic electrophiles
Pena-Lopez, Miguel,Ayan-Varela, Miguel,Sarandeses, Luis A.,Sestelo, Jose Perez
experimental part, p. 1686 - 1694 (2012/03/22)
Aryl and alkenylgold(i) phosphanes react regioselectively with allylic electrophiles such as cinnamyl and geranyl halides (bromide, chloride and acetates) under palladium catalysis in THF at 80 °C to afford the α-substitution product with moderate to high yields. When the reaction is performed with a chiral enantiopure secondary acetate, the α-substituted cross-coupling product is obtained with complete inversion of the stereochemistry.
Stereospecific cross-coupling between alkenylboronates and alkyl halides catalyzed by iron-bisphosphine complexes
Hashimoto, Toru,Hatakeyama, Takuji,Nakamura, Masaharu
experimental part, p. 1168 - 1173 (2012/02/16)
A stereospecific and high-yielding cross-coupling reaction between alkenylboron reagents and alkyl halides is described. The reaction has been achieved by using well-defined iron-bisphosphine complexes such as 1b FeCl 2(3,5-t-Bu2-SciOPP), which was recently developed by the authors' group. Various nonactivated alkyl bromides and chlorides possessing a base/nucleophile-sensitive functional group can participate in the cross-coupling, demonstrating its utility for stereoselective synthesis of functional molecules bearing a carbon-carbon double bond.
Facile coupling of propargylic, allylic and benzylic alcohols with allylsilane and alkynylsilane, and their deoxygenation with Et3SiH, catalyzed by Bi(OTf)3 in [BMIM][BF4] ionic liquid (IL), with recycling and reuse of the IL
Narayana Kumar,Laali, Kenneth K.
experimental part, p. 7347 - 7355 (2012/09/25)
Allyltrimethylsilane (allyl-TMS) reacts with propargylic alcohols 1a-1d in the presence of 10% Bi(OTf)3 in [BMIM][BF4] solvent to furnish the corresponding 1,5-enynes in respectable isolated yields (87-93%) at room temperature. The utility of Bi(OTf)3 as a superior catalyst was demonstrated in a survey study on coupling of allyl-TMS with 1a employing several metallic triflates (Bi, Ln, Al, Yb) as well as, B(C6F 5)3, Zn(NTf2)2 and Bi(NO 3)3·5H2O. Coupling of cyclopropyl substituted propargylic alcohol 1e with allyl-TMS gave the skeletally intact 1,5-enyne and a ring opened derivative as a mixture. Coupling of propargylic/allylic alcohol 1f with allyl-TMS resulted in allylation at both benzylic (2 isomers) and propargylic positions, as major and minor products respectively. The scope of this methodology for allylation of a series of allylic and benzylic alcohols was explored. Chemoselective reduction of a host of propargylic, propagylic/allylic, bis-allylic, allylic, and benzylic alcohols with Et3SiH was achieved in high yields with short reaction times. The same approach was successfully applied to couple representative propargylic and allylic alcohols with 1-phenyl-2-trimethylsilylacetylene. The recovery and reuse of the ionic liquid (IL) was gauged in a case study with minimal decrease in isolated yields after six cycles.
Ni-catalyzed reductive allylation of unactivated alkyl halides with allylic carbonates
Dai, Yijing,Wu, Fan,Zang, Zhenhua,You, Hengzhi,Gong, Hegui
supporting information; experimental part, p. 808 - 812 (2012/02/16)
Game of two electrophiles: Two partially positively charged sp3 carbon atoms can be connected by using a catalytic Ni species in the presence of an environmentally benign Zn reductant, delivering allylated alkanes (see scheme). This unprecedent
