1196-38-9Relevant articles and documents
Green Oxidation of Amines to Imines Based on the Development of Novel Catalytic Systems Using Molecular Oxygen or Hydrogen Peroxide
Marui, Kuniaki,Nomoto, Akihiro,Akashi, Haruo,Ogawa, Akiya
, p. 31 - 42 (2016)
Amines are transformed into the corresponding imines by environmentally benign catalytic oxidation reactions. Gaseous oxygen or hydrogen peroxide is used as the oxidant, and water is the only byproduct. When a vanadium complex is used as the catalyst in an ionic liquid, the amine oxidation successfully proceeds with recycling of the catalyst. Amine oxidation with hydrogen peroxide as an oxidant in water is also attained by using copper(II) sulfate as catalyst. In addition, photoinduced oxidation of amines to imines is conducted by using oxygen as the oxidant in the presence of a zinc-chlorin complex as catalyst.
Visible-Light-Induced Controlled Oxidation of N-Substituted 1,2,3,4-Tetrahydroisoquinolines for the Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones and Isoquinolin-1(2H)-ones
Bansode, Ajay H.,Suryavanshi, Gurunath
, p. 1390 - 1400 (2021)
A visible light-rose bengal-TBHP mediated, controlled oxidation of N-substituted 1,2,3,4-tetrahydroisoquinolines is developed for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and isoquinolin-1(2H)-ones. The present method feature's a broad substrate scope, good functional group tolerances, and the products were prepared in good to excellent yields. The developed methodology further demonstrated in the synthesis of isoindolo[2,1-b] isoquinolin-5(7H)-one (topoisomerase-I inhibitor). (Figure presented.).
Synthesis of novel tricyclic aryltriazole-3-thione compounds
Cai, Cuiman,Plummer, Janet S.,Connor, David,Holsworth, Daniel D.,Edmunds, Jeremy J.
, p. 349 - 356 (2005)
A new synthetic protocol has been developed to provide entry into a series of novel tricyclic aryltriazole-3-thiones analogs. The classical reaction conditions of subjecting an arylhydrazide with thiophosgene to form the thioisocyanate intermediate and ultimately the corresponding aryltriazole-3-thione framework were not successful. However, using a combination of carbon disulfide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to form the thioisocyanate intermediate was found to produce the novel tricyclic aryltriazole-3-thiones (5, 8a-c) in good yield. Copyright Taylor & Francis, Inc.
Unusual dirhodium tetraacetate catalyzed intramolecular cyclization of isoquinoline diazoamides
Chelucci, Giorgio,Culeddu, Nicola,Saba, Antonio,Valenti, Raffaela
, p. 8269 - 8270 (1999)
The dirhodium(II) tetraacetate catalyzed decomposition of an isoquinoline diazoamide leads to the unexpected formation of a 1,3-oxazin-4-one ring which is consistent with a rare example of an intramolecular metal-carbene hydride-abstraction mechanism.
Selective oxidation of benzylic hydrocarbons to carbonyl compounds catalyzed by Mn(III) salen complexes
Lee, Nam Ho,Lee, Chang-Seob,Jung, Duk-Sang
, p. 1385 - 1388 (1998)
Selective oxidation of benzylic hydrocarbons to the carbonyl compounds was achieved using a racemic Mn(III) salen complex 1 as the catalyst. The reaction proceeds in good yields under mild reaction conditions using iodosobenzene or aq. sodium hypochlorite as a stoichiometric oxidant.
Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source
Li, Junxuan,Zhou, Jinlei,Wang, Yumei,Yu, Yue,Liu, Qiang,Yang, Tilong,Chen, Huoji,Cao, Hua
, p. 68 - 74 (2021/11/16)
Pd-catalyzed carbonylation, as an efficient synthetic approach to the installation of carbonyl groups in organic compounds, has been one of the most important research fields in the past decade. Although elegant reactions that allow highly selective carbonylations have been developed, straightforward routes with improved reaction activity and broader substrate scope remain long-term challenges for new practical applications. Here, we show a new type of synergistic Cu/Pd-catalyzed carbonylation reaction using alcohols and dioxgen as the carbonyl sources. A broad range of aryl iodides and alcohols are compatible with this protocol. The reaction is concise and practical due to the ready availability of the starting materials and the scalability of the reaction. In addition, the reaction affords lactones and lactams in an intermolecular fashion. Moreover, DFT calculations have been performed to study the detailed mechanisms. [Figure not available: see fulltext.]
Synthesis of Overloaded Cyclopentadienyl Rhodium(III) Complexes via Cyclotetramerization of tert-Butylacetylene
Kolos, Andrey V.,Nelyubina, Yulia V.,Perekalin, Dmitry S.,Sundararaju, Basker
supporting information, p. 3712 - 3719 (2021/09/18)
Herein we describe the synthesis and reactivity of rhodium catalysts with the very bulky cyclopentadienyl ligand C8H3tBu4 (designated as tBu4Cp). The reaction of [Rh(cod)Cl]2 with tert-butylacetylene in the presence of Et3N gives the complex (tBu4Cp)Rh(cod) (60-65% yield), in which the cyclopentadienyl ligand tBu4Cp is assembled from four alkyne molecules. The oxidation of (tBu4Cp)Rh(cod) with chlorine or bromine gives the corresponding halide complexes (tBu4Cp)RhX2 (X = Cl (85%), Br (95%)), which have unusual 16-electron monomeric structures due to the steric shielding provided by tBu groups. A similar reaction with iodine gives the ionic dinuclear complex [(tBu4Cp)RhI3Rh(tBu4Cp)]I (99%) with halide bridges. The bromide complex (tBu4Cp)RhBr2 reacts with phosphorus ligands such as P(OMe)3, P(OPh)3, PMe2Ph, and PMePh2 to give the 18-electron adducts (tBu4Cp)RhBr2(PR3), but no reaction occurs with larger phosphines such as PPh3. The racemic chloride (tBu4Cp)RhCl2 can be separated into enantiomers by preparative TLC of its diastereomeric adducts with (R)-phenylglycinol. The complex (tBu4Cp)RhBr2 catalyzes C-H activation and annulation of O-pivaloyl-hydroxamate as well as insertion of phenyldiazoacetate into E-H bonds, although the reaction rates and the substrate scope are limited by the bulky tBu4Cp ligand.
