928765-35-9Relevant academic research and scientific papers
Amidation of 1,3-diarylallylic compounds catalysed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone with molecular oxygen as the terminal oxidant
Cheng, Dongping,Zhou, Xiayi,Yuan, Kun,Yan, Jizhong
, p. 127 - 129 (2016)
An efficient amidation has been developed of 1,3-diarylpropenes by carboxamides, sulfonamides, carbamates and anilines catalysed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and benzoyl peroxide with molecular oxygen. The corresponding products were obtai
Nickel(0)-Catalyzed Hydroalkenylation of Imines with Styrene and Its Derivatives
Xiao, Li-Jun,Zhao, Chao-Yue,Cheng, Lei,Feng, Bo-Ya,Feng, Wei-Min,Xie, Jian-Hua,Xu, Xiu-Fang,Zhou, Qi-Lin
supporting information, p. 3396 - 3400 (2018/03/01)
A nickel(0)-catalyzed hydroalkenylation of imines with styrene and its derivatives is described. A wide range of aromatic and aliphatic imines directly coupled with styrene and its derivatives, thus providing various synthetically useful allylic amines with up to 95 % yield. The reaction offers a new atom- and step-economical approach to allylic amines by using alkenes instead of alkenyl-metallic reagents. Experiments and DFT calculations showed that TsNH2 promotes the proton transfer from the coordinated olefin to the imine, accompanied by a new C?C bond formation.
Regioselective Intermolecular Allylic C?H Amination of Disubstituted Olefins via Rhodium/π-Allyl Intermediates
Burman, Jacob S.,Blakey, Simon B.
supporting information, p. 13666 - 13669 (2017/10/24)
A method for catalytic intermolecular allylic C?H amination of trans-disubstituted olefins is reported. The reaction is efficient for a range of common nitrogen nucleophiles bearing one electron-withdrawing group, and proceeds under mild reaction conditions. Good levels of regioselectivity are observed for a wide range of electronically diverse trans-β-alkyl styrene substrates.
Silicon-directed rhenium-catalyzed allylic carbaminations and oxidative fragmentations of γ-silyl allylic alcohols
Chavhan, Sanjay W.,Cook, Matthew J.
supporting information, p. 4891 - 4895 (2014/05/06)
A highly regioselective allylic substitution of β-silyl allylic alcohols has been achieved that provides the branched isomer as a single product. This high level of regiocontrol is achieved through the use of a vinyl silane group that can perform a Hiyama coupling providing 1,3-disubstituted allylic amines. An unusual oxidative fragmentation product was also observed at elevated temperature that appears to proceed by a Fleming-Tamao-type oxidation-elimination pathway.
Direct substitution of hydroxy group of π-activated alcohols with electron-deficient amines using Re2O7 catalyst
Das, Braja Gopal,Nallagonda, Rajender,Ghorai, Prasanta
experimental part, p. 5577 - 5583 (2012/07/31)
The first example of simple Re2O7-catalyzed direct dehydrative coupling between allylic alcohols with electron-deficient amines has been achieved under mild and open flask conditions. The protocol has also been successfully applied t
Mild and efficient allylation of indoles and amides using Amberlyst-15 as a recyclable heterogeneous catalyst
Liu, Zhe,Wang, Dong,Wu, Yanchao,Chen, Yongjun
experimental part, p. 1813 - 1823 (2012/04/10)
A mild and efficient allylation of indoles and amides in the presence of a catalytic amount of Amberlyst-15 has been described in this context. The recyclable heterogeneous catalytic system is practical and facile for the synthesis of C- and N-allylated d
FeCl3·6H2O and TfOH as catalysts for allylic amination reaction: A comparative study
Trillo, Paz,Baeza, Alejandro,Najera, Carmen
experimental part, p. 2929 - 2934 (2012/06/29)
The use of FeCl3·6H2O and TfOH as readily available and easy-to-handle catalysts for the direct allylic amination reaction using a wide variety of nitrogenated nucleophiles onto different free allylic alcohols is described. Comparative studies between these catalysts, as representative Lewis and Bronsted acids are conducted, concluding that both are suitable catalysts for this transformation. The reactions are performed in a flask open to air and using technical grade 1,4-dioxane. In light of the results obtained from this study it can be asserted that TfOH turned out to be slightly superior than the FeIII salt since similar or better yields are obtained in most of the cases using lower catalyst loadings and milder reaction conditions. A similar trend is observed when carbonucleophiles were employed in the allylic substitution reaction. Studies for the elucidation of the reaction mechanism are in agreement with a carbocationic intermediate, being the regioselectivity governed by the stability of the final product. Copyright
Aluminum triflate as a powerful catalyst for direct amination of alcohols, including electron-withdrawing group-substituted benzhydrols
Ohshima, Takashi,Ipposhi, Junji,Nakahara, Yasuhito,Shibuya, Ryozo,Mashima, Kazushi
supporting information, p. 2447 - 2452 (2012/11/07)
Direct aminations of allylic alcohols, benzylic alcohols, and benzhydrols with electron-withdrawing (F, Br, I, NO2, or CN) substituents were efficiently catalyzed by aluminum triflate [Al(OTf)3] to afford the corresponding biarylamines in high yield, and the dibromo-substituted product was further transformed into letrozole. Copyright
Fluorinated alcohols as promoters for the metal-free direct substitution reaction of allylic alcohols with nitrogenated, silylated, and carbon nucleophiles
Trillo, Paz,Baeza, Alejandro,Najera, Carmen
, p. 7344 - 7354 (2012/10/30)
The direct allylic substitution reaction using allylic alcohols in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and 2,2,2-trifluoroethanol (TFE) as reaction media is described. The developed procedure is simple, works under mild conditions (rt, 50 and 70 °C), and proves to be very general, since different nitrogenated nucleophiles and carbon nucleophiles can be used achieving high yields, especially when HFIP is employed as solvent and aromatic allylic alcohols are the substrates. Thus, sulfonamides, carbamates, carboxamides, and amines can be successfully employed as nitrogen-based nucleophiles. Likewise, silylated nucleophiles such as trimethylsilylazide, allyltrimethylsilane, trimethylsilane, and trimethylsilylphenylacetylene give the corresponding allylic substitution products in high yields. Good results for the Friedel-Crafts adducts are also achieved with aromatic compounds (phenol, anisole, indole, and anilines) as nucleophiles. Particularly interesting are the results obtained with electron-rich anilines, which can behave as nitrogenated or carbon nucleophiles depending on their electronic properties and the solvent employed. In addition, 1,3-dicarbonyl compounds (acetylacetone and Meldrum's acid) are also successfully employed as soft carbon nucleophiles. Studies for mechanism elucidation are also reported, pointing toward the existence of carbocationic intermediates and two working reaction pathways for the obtention of the allylic substitution product.
Direct substitution of the hydroxy group with highly functionalized nitrogen nucleophiles catalyzed by Au(III)
Ohshima, Takashi,Nakahara, Yasuhito,Ipposhi, Junji,Miyamoto, Yoshiki,Mashima, Kazushi
supporting information; experimental part, p. 8322 - 8324 (2011/09/15)
A direct catalytic substitution of various allylic and benzylic alcohols with synthetically useful, but acid-sensitive Boc, Bus, and Dios protected amine nucleophiles, which have not been well utilized for Lewis acid catalysis, with various functionalities (OTBS, OTHP, etc.) was efficiently catalyzed by 1 mol% of Au(iii) under mild conditions.
