6908-67-4Relevant academic research and scientific papers
Iridium-Catalyzed β-C(sp2)?H Borylation of Enamides – Access to 3,3-Dihalogeno-2-methoxypiperidines
Gillaizeau, Isabelle,Dondasse, Isma?l,Nicolas, Cyril,Mimoun, Liliane,Sukach, Volodymyr,Meudal, Hervé
supporting information, (2022/02/07)
An efficient catalytic preparation of synthetically useful new β-borylated enamides was achieved under relatively mild conditions via a regioselective iridium-catalyzed C(sp2)?H borylation. The method features broad substrate scope, good functi
Phosphine-Catalyzed Vinylation at Low Acetylene Pressure
Bienewald, Frank,Comba, Peter,Hashmi, A. Stephen K.,Menche, Maximilian,Rominger, Frank,Schafer, Ansgar,Schaub, Thomas,Sitte, Nikolai A.,Tuzina, Pavel
, p. 13041 - 13055 (2021/09/18)
The vinylation of various nucleophiles with acetylene at a maximum pressure of 1.5 bar is achieved by organocatalysis with easily accessible phosphines like tri-n-butylphosphine. A detailed mechanistic investigation by quantum-chemical and experimental methods supports a nucleophilic activation of acetylene by the phosphine catalyst. At 140 °C and typically 5 mol % catalyst loading, cyclic amides, oxazolidinones, ureas, unsaturated cyclic amines, and alcohols were successfully vinylated. Furthermore, the in situ generation of a vinyl phosphonium species can also be utilized in Wittig-type functionalization of aldehydes.
Anti-Markovnikov stereoselective hydroamination and hydrothiolation of (hetero)aromatic alkynes using a metal-free cyclic trimeric phosphazene base
Zhao, Na,Lin, Chengdong,Wen, Lirong,Li, Zhibo
, p. 3432 - 3440 (2019/05/15)
Hydroamination and hydrothiolation are the most efficient and completely atom-economical process to construct important enamine and vinyl sulfide intermediates in pharmaceutical and organic chemistry. The cyclic trimeric phosphazene base (CTPB) showed gre
Palladium-Catalyzed Markovnikov-Selective Hydroselenation of N-Vinyl Lactams with Selenols Affording N,Se-Acetals
Tamai, Taichi,Yoshikawa, Megumi,Higashimae, Shinya,Nomoto, Akihiro,Ogawa, Akiya
, p. 324 - 329 (2016/01/15)
The highly regioselective hydroselenation of N-vinyl lactams has been revealed to successfully afford the corresponding N,Se-acetals as Markovnikov adducts. In the case of terminal N-vinyl lactams, Markovnikov-selective hydroselenation proceeds efficiently in the absence of any catalyst (or additive), owing to the acidity of the selenols. In contrast, the self-promoted hydroselenation is inefficient with internal N-vinyl lactams. In the presence of palladium diacetate (Pd(OAc)2), however, the desired hydroselenation of internal N-vinyl lactams proceeds efficiently to afford the corresponding N,Se-acetals.
Regioselective hydrothiolation of alkenes bearing heteroatoms with thiols catalyzed by palladium diacetate
Tamai, Taichi,Ogawa, Akiya
, p. 5028 - 5035 (2014/06/23)
In sharp contrast to many examples of transition-metal-catalyzed hydrothiolation of alkynes, the corresponding catalytic addition of thiols to alkenes has remained undeveloped. However, a novel Pd-catalyzed addition of thiols to alkenes bearing a heteroatom, such as oxygen and nitrogen, is found to proceed under mild conditions to give the corresponding Markovnikov adducts, regioselectively, in good yields.
TFA-catalyzed C-N bond activation of enamides with indoles: Efficient synthesis of 3,3-bisindolylpropanoates and other bisindolylalkanes
Xu, Hai-Yan,Zi, You,Xu, Xiao-Ping,Wang, Shun-Yi,Ji, Shun-Jun
, p. 1600 - 1605 (2013/02/25)
An efficient TFA-catalyzed cleavage of C-N bonds in alkylation of indoles by tertiary enamides was described. A variety of bisindolylalkane derivatives, especially 3,3-bisindolylpropanoates, were expeditiously synthesized in good yields.
Arylations of substituted enamides by aryl iodides: Regio- and stereoselective synthesis of (z)-β-amido-β-arylacrylates
Gou, Quan,Deng, Bin,Zhang, Hongbin,Qin, Jun
supporting information, p. 4604 - 4607 (2013/09/24)
Arylations of substituted enamides by aryl iodides were achieved for the first time via an unusual PdCl2(COD)/Ag3PO4 catalytic system. A broad range of (Z)-β-amido-β-arylacrylates were prepared regio- and stereoselectively in a highly efficient manner.
The aminocyclodextrin/Pd(OAc)2 complex as an efficient catalyst for the Mizoroki-Heck cross-coupling reaction
Kanagaraj, Kuppusamy,Pitchumani, Kasi
supporting information, p. 14425 - 14431 (2013/11/06)
An aminocyclodextrin/Pd(OAc)2 complex is used as an efficient, reusable catalyst in the Mizoroki-Heck reaction of aryl halides/triflates with olefins to give carbon-carbon-coupled products in good to excellent yields. This simple, efficient catalytic system is applicable to a wide range of aryl and heteroaryl halides/triflates and olefins. This environmentally benign procedure is less hazardous, milder, uses a catalytic amount of ligand and Pd(OAc) 2, avoids an inert atmosphere, and catalyst recovery and reusability are achieved. Copyright
Synthesis of sterically hindered enamides via a Ti-mediated condensation of amides with aldehydes and ketones
Genovino, Julien,Lagu, Bharat,Wang, Yaping,Toure, B. Barry
supporting information; experimental part, p. 6735 - 6737 (2012/08/07)
The first TiCl4-mediated condensation of secondary amides with aldehydes and ketones has been achieved. The reaction proceeds at room temperature and is complete within 5 h in most cases. The optimized procedure used 5 equiv of an amine base hi
Direct C-H functionalization of enamides and enecarbamates by using visible-light photoredox catalysis
Jiang, Heng,Huang, Chengmei,Guo, Jiajia,Zeng, Chuanqi,Zhang, Yan,Yu, Shouyun
, p. 15158 - 15166 (2013/01/15)
Direct C-H functionalization of various enamides and enecarbamates was realized through visible-light photoredox catalyzed reactions. Under the optimized conditions using [Ir(ppy)2(dtbbpy)PF6] as photocatalyst in combination with Na
