55487-54-2Relevant academic research and scientific papers
Copper-promoted difunctionalization of unactivated alkenes with silanes
Chen, Xiaoyu,Guo, Zhuangzhuang,Li, Jingya,Wu, Yangjie,Wu, Yusheng,Xue, Yingying,Zou, Dapeng
, p. 989 - 994 (2022/02/11)
An efficient copper-catalyzed cascade difunctionalization of N-allyl anilines toward the synthesis of silylated indolines using commercially available silanes has been reported. This strategy provides a new avenue for the synthesis of a diverse array of i
A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C?C Coupling in Air
Kundu, Gourab,Rissanen, Kari,Schoenebeck, Franziska,Sperger, Theresa
supporting information, p. 21930 - 21934 (2020/10/02)
We report a new air-stable PdI dimer, [Pd(μ-I)(PCy2tBu)]2, which triggers E-selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C?C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C?Br, C?OTf/OFs, and C?Cl bonds in poly(pseudo)halogenated arenes, displaying superior activity over previous PdI dimer generations for substrates that bear substituents ortho to C?OTf.
Nickel(0)-Catalyzed N-Allylation of Amides and p-Toluenesulfonamide with Allylic Alcohols under Neat and Neutral Conditions
Azizi, Mohamed Salah,Edder, Youssef,Karim, Abdallah,Sauthier, Mathieu
, p. 3796 - 3803 (2016/08/16)
Nickel(0)-catalyzed direct N-allylation of amides and p-toluenesulfonamide with allylic alcohols took place in the presence of Ni0–diphosphine complexes. The corresponding N-allylated (and/or N,N-diallylated) products were obtained in moderate to high yields under neutral conditions.
Generation and trapping of ketenes in flow
Henry, Cyril,Bolien, David,Ibanescu, Bogdan,Bloodworth, Sally,Harrowven, David C.,Zhang, Xunli,Craven, Andy,Sneddon, Helen F.,Whitby, Richard J.
, p. 1491 - 1499 (2015/03/04)
Ketenes were generated by the thermolysis of alkoxyalkynes under flow conditions, and then trapped with amines and alcohols to cleanly give amides and esters. For a 10 min reaction time, temperatures of 180, 160, and 140 °C were required for >95% conversion of EtO, iPrO, and tBuO alkoxyalkynes, respectively. Variation of the temperature and flow rate with inline monitoring of the output by IR spectroscopy allowed the kinetic parameters for the conversion of 1-ethoxy-1-octyne to be easily estimated (Ea = 105.4 kJ/mol). Trapping of the in-situ-generated ketenes by alcohols to give esters required the addition of a tertiary amine catalyst to prevent competitive [2+2] addition of the ketene to the alkoxyalkyne precursor.
Metal-free reductive cleavage of C-N and S-N bonds by photoactivated electron transfer from a neutral organic donor
O'Sullivan, Steven,Doni, Eswararao,Tuttle, Tell,Murphy, John A.
supporting information, p. 474 - 478 (2014/01/23)
A photoactivated neutral organic super electron donor cleaves challenging arenesulfonamides derived from dialkylamines at room temperature. It also cleaves a)ArC-NR and b)ArN-C bonds. This study also highlights the assistance given to these cleavage reactions by the groups attached to N in (a) and to C in (b), by lowering LUMO energies and by stabilizing the products of fragmentation. Radical fragmentations: Electron transfer from the photoactivated neutral electron donor 1 delivers high yields of S-N and C-N cleavage products for a range of nitrogen-containing species. These reactions proceed at room temperature and under mild reaction conditions in the absence of any metal reagents. DMF=N,N-dimethylformamide, Ts=4-toluenesulfonyl.
Visible-light-induced photocatalytic reductive transformations of organohalides
Kim, Hyejin,Lee, Chulbom
, p. 12303 - 12306 (2013/02/23)
A photo opportunity: A visible-light-excited iridium catalyst delivers electrons from an amine to an organohalide. The electron transfer then induces reductive scission of the carbon-halogen bond, generating the corresponding alkyl, alkenyl, and aryl radical that can undergo cyclization and hydrodehalogenation reactions. Copyright
Highly efficient and regioselective allylic amination of allylic alcohols catalyzed by [Mo3PdS4] cluster
Tao, Yinsong,Zhou, Yuhan,Qu, Jingping,Hidai, Masanobu
experimental part, p. 1982 - 1984 (2010/06/21)
A highly efficient and regioselective allylation reaction of amines with allylic alcohols under mild conditions catalyzed by the cubane-type sulfido cluster [(Cp*Mo)3S4Pd(dba)][PF6] with H3BO3 as an additive has been developed. A variety of amines and allylic alcohols are investigated, and in the case of allylic alcohols bearing substituents at either α- or γ-position only linear allylic amination products are obtained.
Highly efficient and regioselective allylation with allylic alcohols catalyzed by [Mo3S4Pd(η3-allyl)] clusters
Tao, Yinsong,Wang, Bo,Wang, Baomin,Qu, Lihong,Qu, Jingping
experimental part, p. 2726 - 2729 (2010/08/06)
(Figure presented) A highly efficient and regioselective allylation reaction of amines and active methylene compounds directly using allylic alcohols under mild conditions catalyzed by the novel cubane-type sulfido [(CpMo)3(μ3-S)4Pd(η3-allyl)] [PF6]2 clusters has been developed. A variety of allylic alcohols and nucleophiles including amines and active methylene compounds are investigated, and in the case of allylic alcohols bearing substituents at either the α- or γ-position only linear products are obtained.
Synthesis of heterocyclic compounds by ring-closing metathesis (RCM): Preparation of oxygenated or nitrogenated compounds
Sanchez, Isabel,Pujol, Maria Dolors
, p. 1823 - 1828 (2007/10/03)
Novel methods for heterocyclic synthesis by metathesis have been developed. Versatile heterocyclic compounds were easily prepared in good yield from intermediate olefins by ring-closing olefin metathesis using the catalyst dichloro(benzylidene)bis(tricycl
Highly selective synthesis of (E)-N-aryl-N-(1-propenyl) ethanamides via isomerization of N-allyl ethanamides catalyzed by ruthenium complexes
Krompiec, Stanislaw,Pigulla, Mariola,Szczepankiewicz, Wojciech,Bieg, Tadeusz,Kuznik, Nikodem,Leszczynska-Sejda, Katarzyna,Kubicki, Maciej,Borowiak, Teresa
, p. 7095 - 7098 (2007/10/03)
A convenient and highly selective method of synthesis of (E)-N-aryl-N-(1-propenyl)ethanamides via isomerization of respective N-allyl-N-arylethanamides catalyzed by [RuClH(CO)(PPh3)3] has been described. N-Allyl-N-arylethanamides hav
