41882-49-9Relevant academic research and scientific papers
Half-Sandwich Ruthenium Complexes Bearing Hemilabile κ2-(C,S)?Thioether-Functionalized NHC Ligands: Application to Amide Synthesis from Alcohol and Amine
Achard, Thierry,Bellemin-Laponnaz, Stéphane,Chen, Weighang,Egly, Julien,Maisse-Fran?ois, Aline
supporting information, (2022/01/20)
Amide synthesis is one of the most crucial transformations in chemistry and biology. Among various catalytic systems, N-heterocyclic carbene (NHC)-based ruthenium (Ru) catalyst systems have been proven to be active for direct synthesis of amides by sustainable acceptorless dehydrogenative Coupling of primary alcohols with amines. Most often, these catalytic systems usually use monodentate NHC and thus require an additional ligand to obtain high reactivity and selectivity. In this work, a series of cationic Ru(II)(η6-p-cymene) complexes with thioether-functionalized N-heterocyclic carbene ligands (imidazole and benzimidazole-based) have been prepared and fully characterized. These complexes have then been used in the amidation reaction and the most promising one (i. e. 3 c) has been applied on a large range of substrates. High conversions albeit with moderate yields have generally been obtained.
A General Way to Construct Arene-Fused Seven-Membered Nitrogen Heterocycles
Bakulina, Olga,Chizhova, Maria,Dar'in, Dmitry,Krasavin, Mikhail
, p. 362 - 371 (2018/01/27)
Imines react with seven-membered cyclic anhydrides (prepared from the corresponding dicarboxylic acids by a recently discovered in-situ cyclodehydration protocol) by the Castagnoli–Cushman reaction pathway to give privileged seven-membered arene-fused nitrogen-heterocyclic compounds with reagent-controlled diversity of the skeleton and peripheral groups.
Skeletal Diversity in Combinatorial Fashion: A New Format for the Castagnoli-Cushman Reaction
Lepikhina, Anastasia,Dar'In, Dmitry,Bakulina, Olga,Chupakhin, Evgeny,Krasavin, Mikhail
, p. 702 - 707 (2017/11/20)
A new format for the Castagnoli-Cushman reaction of structurally diverse dicarboxylic acids, amines, and aldehydes in the presence of acetic anhydride as dehydrating agent is described. The reaction is distinctly amenable to parallel format: the combinato
Direct Synthesis of Amides by Dehydrogenative Coupling of Amines with either Alcohols or Esters: Manganese Pincer Complex as Catalyst
Kumar, Amit,Espinosa-Jalapa, Noel Angel,Leitus, Gregory,Diskin-Posner, Yael,Avram, Liat,Milstein, David
supporting information, p. 14992 - 14996 (2017/10/25)
The first example of base-metal-catalysed synthesis of amides from the coupling of primary amines with either alcohols or esters is reported. The reactions are catalysed by a new manganese pincer complex and generate hydrogen gas as the sole byproduct, thus making the overall process atom-economical and sustainable.
Dual Heterogeneous Catalyst Pd-Au@Mn(II)-MOF for One-Pot Tandem Synthesis of Imines from Alcohols and Amines
Chen, Gong-Jun,Ma, Hui-Chao,Xin, Wen-Ling,Li, Xiao-Bo,Jin, Fa-Zheng,Wang, Jing-Si,Liu, Ming-Yang,Dong, Yu-Bin
supporting information, p. 654 - 660 (2017/01/13)
A new Mn(II) metal-organic framework (MOF) 1 was synthesized by the combination of 4,4,4-trifluoro-1-(4-(pyridin-4-yl)phenyl)butane-1,3-dione (L) and Mn(OAc)2 in solution. 1 features a threefold-interpenetrating NbO net containing honeycomb-like channels, in which the opposite Mn(II)···Mn(II) distance is 23.5075(10) ?. Furthermore, 1 can be an ideal platform to support Pd-Au bimetallic alloy nanoparticles to generate a composite catalytic system of Pd-Au@Mn(II)-MOF (2). 2 can be a highly active bifunctional heterogeneous catalyst for the one-pot tandem synthesis of imines from benzyl alcohols and anilines and from benzyl alcohols and benzylamines.
Simple, chemoselective, and diastereoselective Reformatsky-type synthesis of α-bromo-α-fluoro-β-lactams
Tarui, Atsushi,Kawashima, Naoto,Sato, Kazuyuki,Omote, Masaaki,Miwa, Yoshihisa,Minami, Hideki,Ando, Akira
supporting information; experimental part, p. 2000 - 2003 (2010/06/21)
The chemoselective and diastereoselective synthesis of syn-α-bromo-α-fluoro-β-lactams was achieved using the diethylzinc-mediated Reformatsky-type reaction of ethyl dibromofluoroacetate with imines. The reaction led to diastereomerically pure β-lactams in good to moderate yields (up to 78% yield) with only small amounts of aziridine derivatives. Noncyclized 3-amino-2-bromo-2-fluoro carboxylic esters, usual Reformatsky adducts, were not formed. In contrast, reactions carried out under typical Reformatsky conditions using zinc metal were poorly chemoselective, leading to mixtures of β-lactams and aziridine derivatives.
