Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in   situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst

2020 ◽  
Vol 362 (17) ◽  
pp. 3583-3588 ◽  
Author(s):  
Tatsuki Utsumi ◽  
Kenta Noda ◽  
Daichi Kawauchi ◽  
Hirofumi Ueda ◽  
Hidetoshi Tokuyama
Keyword(s):  
Ammonium Salt ◽  
Aerobic Oxidation ◽  
Primary Amines ◽  
Grubbs Catalyst

scholarly journals Metal-Free Air Oxidation in a Convenient Cascade Approach for the Access to Isoquinoline-1,3,4(2H)-triones

Molecules ◽  
2019 ◽  
Vol 24 (11) ◽  
pp. 2177
Author(s):  
Antonia Di Mola ◽  
Consiglia Tedesco ◽  
Antonio Massa
Keyword(s):  
Heterocyclic Compounds ◽  
Aromatic Ketone ◽  
Primary Amines ◽  
Cascade Process ◽  
Staudinger Reaction ◽  
Caspase Inhibitor ◽  
Air Oxidation ◽  
Metal Free ◽  
Free Air

Herein we describe a very useful application of the readily available trifunctional aromatic ketone methyl-2-(2-bromoacetyl)benzoate in reactions with primary amines. An unexpected in situ air oxidation that follows a cascade process allowed the access to a series of isoquinoline-1,3,4(2H)-triones, a class of heterocyclic compounds of great interest containing an oxygen-rich heterocyclic scaffold. A modification of the original protocol, utilizing a Staudinger reaction in the presence of trimethylphosphine, was necessary for the synthesis of Caspase inhibitor trione with free NH group.

On the selective aerobic oxidation of benzyl alcohol with Pd/Au-nanoparticles in batch and flow

2014 ◽  
Vol 3 (1) ◽  
pp. 99-110 ◽  
Author(s):  
Hannes Alex ◽  
Norbert Steinfeldt ◽  
Klaus Jähnisch ◽  
Matthias Bauer ◽  
Sandra Hübner
Keyword(s):  
Catalytic Activity ◽  
Benzyl Alcohol ◽  
Aerobic Oxidation ◽  
X Ray ◽  
X Ray Scattering ◽  
Oxidation Of Benzyl Alcohol ◽  
Transmission Electron ◽  
Vis Spectroscopy ◽  
Selective Aerobic Oxidation

AbstractNanoparticles (NP) have specific catalytic properties, which are influenced by parameters like their size, shape, or composition. Bimetallic NPs, composed of two metal elements can show an improved catalytic activity compared to the monometallic NPs. We, herein, report on the selective aerobic oxidation of benzyl alcohol catalyzed by unsupported Pd/Au and Pd NPs at atmospheric pressure. NPs of varying compositions were synthesized and characterized by UV/Vis spectroscopy, transmission electron microscopy (TEM), and small-angle X-ray scattering (SAXS). The NPs were tested in the model reaction regarding their catalytic activity, stability, and recyclability in batch and continuous procedure. Additionally, in situ extended X-ray absorption fine structure (EXAFS) measurements were performed in order to get insight in the process during NP catalysis.

Aerobic Oxidation of Primary Amines to Amides Catalyzed by an Annulated Mesoionic Carbene (MIC) Stabilized Ru Complex

2021 ◽  
Author(s):  
Jitendra K Bera ◽  
Suman Yadav ◽  
Noor U Din Reshi ◽  
Saikat Pal
Keyword(s):  
Aerobic Oxidation ◽  
Primary Amines ◽  
Ru Complex

Catalytic aerobic oxidation of primary amines to the amides, using the precatalyst [Ru(COD)(L1)Br2] (1) bearing an annulated π−conjugated imidazo[1,2−a][1,8]naphthyridine-based mesoionic carbene ligand L1, is disclosed. This catalytic protocol is distinguished...

Functional Group Protection

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Secondary Amines ◽  
Primary Amines ◽  
Silyl Ether ◽  
Southern Illinois ◽  
Convenient Procedure ◽  
North Eastern ◽  
National University ◽  
Facile Preparation ◽  
The University

Bekington Myrboh of North-Eastern Hill University reported (Tetrahedron Lett. 2010, 51, 2862) a convenient procedure for the oxidative removal of a 1,3-oxathiolane 1 or a 1,3-dithiolane. Sang-Gyeong Lee and Yong-Jin Yoon of Gyeongsang National University developed (J. Org. Chem. 2010, 75, 484) the pyridazin-3(2H )-one 4 for the microwave-mediated deprotection of an oxime 3. Dario M. Bassani of Université Bordeaux 1 and John S. Snaith of the University of Birmingham devised (J. Org. Chem. 2010, 75, 4648) a procedure for the facile preparation of esters such as 6. Brief photolysis (350 nm) returned the parent carboxylic acid 7. Craig M. Williams of the University of Queensland prepared (Tetrahedron Lett. 2010, 51, 1158) the trithioorthoester 8 by iterative opening of epichlorohydrin. He found that the keto ester 9 could be efficiently released by Hg-mediated hydrolysis. Masatoshi Mihara of the Osaka Municipal Technical Research Institute established (Synlett 2010, 253) that even very congested alcohols such as 10 could be acetylated by acetic anhydride containing a trace of FeCl3. Colleen N. Scott, now at Southern Illinois University, developed (J. Org. Chem. 2010, 75, 253) a convenient procedure for the preparation of the hydridosilane 13, which on Mn catalysis added the alcohol 12 to make the unsymmetrical bisalkoxysilane 14. Sabine Berteina-Raboin of the Université d’Orléans found (Tetrahedron Lett. 2010, 51, 2115) that NaBH4 in EtOH cleanly removed the chloroacetates from 15. Both other esters and silyl ethers were stable under these conditions. Ram S. Mohan of Illinois Wesleyan University established (Tetrahedron Lett. 2010, 51, 1056) that Fe(III) tosylate in methanol selectively removed the alkyl silyl ether from 17 without affecting the aryl silyl ether. Alakananda Hajra and Adinath Majee of Visva-Bharati University effected (Tetrahedron Lett. 2010, 51, 2896) formylation of an amine 19 by heating with commercial 85% formic acid as the solvent in a sealed tube at 80°C. Although both primary and secondary amines could be effi ciently formylated, the primary amines were much more reactive. Doo Ok Jang of Yonsei University found (Tetrahedron Lett. 2010, 51, 683) that the conveniently handled CF3CCO2H (the acid chloride is a gas) could be activated in situ to selectively convert 22 into 24.

scholarly journals A dual biomimetic process for the selective aerobic oxidative coupling of primary amines using pyrogallol as a precatalyst. Isolation of the [5 + 2] cycloaddition redox intermediates

2020 ◽  
Vol 22 (6) ◽  
pp. 1894-1905 ◽  
Author(s):  
Martine Largeron ◽  
Patrick Deschamps ◽  
Karim Hammad ◽  
Maurice-Bernard Fleury
Keyword(s):  
Oxidative Coupling ◽  
Low Cost ◽  
Primary Amines ◽  
Processing Step

Low-cost pyrogallol precatalyst undergoes an oxidative self-processing step for delivering the active organocatalyst in situ through a dual biomimetic process.

Metal-Free Oxidative C(sp3)–N Coupling by HBr and DMSO: A Novel Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 912-917 ◽  
Author(s):  
Parviz Ranjbar ◽  
Narjes Rezaei ◽  
Ehsan Sheikhi
Keyword(s):  
Oxidative Cyclization ◽  
Cyclization Reaction ◽  
Primary Amines ◽  
Isatoic Anhydride ◽  
Reaction Conditions ◽  
Coupling Process ◽  
Benzylic Alcohols ◽  
Metal Free ◽  
Novel Synthesis

A metal-free oxidative C(sp3)–N coupling process has been developed for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones. The reaction between primary amines, isatoic anhydride, and benzylic alcohols in the presence of HBr in DMSO at 80 °C affords 2,3-dihydroquinazolin-4(1H)-ones in excellent yields. Under these reaction conditions, benzylic alcohols react with in situ generated bromodimethylsulfonium bromide to form alkoxysulfonium intermediates. These intermediates undergo an oxidative cyclization reaction with primary amines and isatoic anhydride to produce the title products.

scholarly journals Catalytic C(sp3 )−H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ

2016 ◽  
Vol 55 (31) ◽  
pp. 9084-9087 ◽  
Author(s):  
Yan Xu ◽  
Michael C. Young ◽  
Chengpeng Wang ◽  
David M. Magness ◽  
Guangbin Dong
Keyword(s):  
Primary Amines ◽  
Directing Group

Aerobic Oxidation of Primary Amines to Oximes Catalyzed by DPPH and WO3/Al2O3

2008 ◽  
Vol 47 (11) ◽  
pp. 2079-2081 ◽  
Author(s):  
Ken Suzuki ◽  
Tomonari Watanabe ◽  
Shun-Ichi Murahashi
Keyword(s):  
Aerobic Oxidation ◽  
Primary Amines

scholarly journals First in situ vesicular self-assembly of ‘binols’ generated by a two-component aerobic oxidation reaction

RSC Advances ◽  
2018 ◽  
Vol 8 (51) ◽  
pp. 29155-29163 ◽  
Author(s):  
Braja G. Bag ◽  
Subrata Ghorai ◽  
Saikat K. Panja ◽  
Shaishab K. Dinda ◽  
Koushik Paul
Keyword(s):  
Self Assembly ◽  
Oxidation Reaction ◽  
Aerobic Oxidation ◽  
Alkyl Chains ◽  
Two Component ◽  
Donor Acceptor ◽  
Self Assembled ◽  
Naphthol Derivatives

Binol derivatives, obtained by aerobic coupling of two 2-naphthol derivatives having H-bond donor–acceptor groups and appended alkyl chains, spontaneously self-assembled in situ yielding vesicular self-assemblies and gels.

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