Propargylation of 1,3-dicarbonyl compounds catalyzed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and sodium nitrite in the presence of molecular oxygen and formic acid

RSC Advances ◽  
2016 ◽  
Vol 6 (57) ◽  
pp. 52459-52463 ◽  
Author(s):  
Dongping Cheng ◽  
Xiayi Zhou ◽  
Xiaoliang Xu ◽  
Jizhong Yan
Keyword(s):  
Formic Acid ◽  
Molecular Oxygen ◽  
Sodium Nitrite ◽  
Coupling Reaction ◽  
Dicarbonyl Compounds ◽  
Terminal Oxidation

The coupling reaction of 1,3-diarylpropyne and 1,3-dicarbonyl compounds using molecular oxygen as a terminal oxidation was developed. Catalyzed by DDQ and NaNO2 in the presence of HCOOH, the corresponding products were obtained in 37–87% yields.

An Unprecedented Cyano-Induced Sodium Nitrite-Catalyzed C(sp3)-H and C(sp2)-H Coupling Reaction

2018 ◽  
Vol 15 (7) ◽  
pp. 989-994 ◽  
Author(s):  
Ling Li ◽  
Bo Su ◽  
Yuxiu Liu ◽  
Qingmin Wang
Keyword(s):  
Sodium Nitrite ◽  
Oxidative Coupling ◽  
High Resolution Mass Spectrometry ◽  
Coupling Reaction ◽  
13C Nmr Spectroscopy ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
1H And 13C Nmr ◽  
Oxidative Coupling Reaction ◽  
Oxidative Coupling Reactions

Aim and Objective: During the investigation of sodium nitrite-catalyzed oxidative coupling reaction of aryls, an unprecedented C(sp2)-H and C(sp3)-H coupling of substituted 2-aryl acetonitrile was found. Materials and Methods: The structure of the coupled product was confirmed by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry (HRMS), and comparison of its derivatives with known compounds. The effects of methoxy group in the benzene ring on the reaction were evaluated. Results: The optimized reaction conditions are summarized as follows: CF3SO3H/substrate = 1.5 equiv., NaNO2/substrate = 0.3 equiv., CH3CN as solvent. 2-(4-Methoxyphenyl)acetonitrile and 2-(3,4,5- trimethoxyphenyl)acetonitrile could also generate C(sp2)-H and C(sp3)-H coupling. The coupling reaction occurred as a typical radial mechanism. Conclusion: An unprecedented cyano-induced, NaNO2-catalyzed oxidative C(sp3)-H and C(sp2)-H coupling was reported. The reaction proceeded under very mild conditions, using O2 in the air as terminal oxidant. The unique oxidative manner might provide more inspiration for the development of intriguing oxidative coupling reactions.

scholarly journals Crystallization and preliminary X-ray characterization of the 2,4′-dihydroxyacetophenone dioxygenase fromAlcaligenessp. 4HAP

2014 ◽  
Vol 70 (6) ◽  
pp. 823-826 ◽  
Author(s):  
G. Beaven ◽  
A. Bowyer ◽  
P. Erskine ◽  
S. P. Wood ◽  
A. McCoy ◽  
...  
Keyword(s):  
Synchrotron Radiation ◽  
Formic Acid ◽  
Molecular Oxygen ◽  
Aromatic Ring ◽  
Bond Cleavage ◽  
Its Sequence ◽  
Hydroxybenzoic Acid ◽  
X Ray

The enzyme 2,4′-dihydroxyacetophenone dioxygenase (or DAD) catalyses the conversion of 2,4′-dihydroxyacetophenone to 4-hydroxybenzoic acid and formic acid with the incorporation of molecular oxygen. Whilst the vast majority of dioxygenases cleave within the aromatic ring of the substrate, DAD is very unusual in that it is involved in C—C bond cleavage in a substituent of the aromatic ring. There is evidence that the enzyme is a homotetramer of 20.3 kDa subunits each containing nonhaem iron and its sequence suggests that it belongs to the cupin family of dioxygenases. By the use of limited chymotrypsinolysis, the DAD enzyme fromAlcaligenessp. 4HAP has been crystallized in a form that diffracts synchrotron radiation to a resolution of 2.2 Å.

Pd/C-Catalyzed Direct α-Oxygenation of 1,3-Dicarbonyl Compounds Using Molecular Oxygen

Synlett ◽  
2008 ◽  
Vol 2008 (15) ◽  
pp. 2291-2294 ◽  
Author(s):  
Hironao Sajiki ◽  
Yasunari Monguchi ◽  
Tohru Takahashi ◽  
Yusuke Iida ◽  
Yuta Fujiwara ◽  
...  
Keyword(s):  
Molecular Oxygen ◽  
Dicarbonyl Compounds

Copper-catalyzed highly diastereoselective cross-dehydrogenative coupling between 8-hydroxyisochromanes and 1,3-dicarbonyl compounds

2019 ◽  
Vol 6 (13) ◽  
pp. 2275-2279 ◽  
Author(s):  
Zhen Zhang ◽  
Yong-Qiang Tu ◽  
Xiao-Ming Zhang ◽  
Fu-Min Zhang ◽  
Shao-Hua Wang
Keyword(s):  
Coupling Reaction ◽  
Dicarbonyl Compounds ◽  
Dehydrogenative Coupling

A novel copper-catalyzed highly diastereoselective cross-dehydrogenative coupling reaction for the access of tricyclic chromanes from 8-hydroxyisochromanes and 1,3-dicarbonyl compounds.

Catalytic oxidation of cellulose to formic acid in H5PV2Mo10O40 + H2SO4 aqueous solution with molecular oxygen

2016 ◽  
Vol 18 (17) ◽  
pp. 4725-4732 ◽  
Author(s):  
Ting Lu ◽  
Muge Niu ◽  
Yucui Hou ◽  
Weize Wu ◽  
Shuhang Ren ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Formic Acid ◽  
Catalytic Oxidation ◽  
Molecular Oxygen ◽  
Heteropoly Acid ◽  
Ph Modifier ◽  
H2so4 Aqueous Solution

In this work, the most frequently-used heteropoly acid H5PV2Mo10O40 was employed with a pH “modifier” of H2SO4 in aqueous solution for the catalytic oxidation of cellulose to formic acid.

Efficient Oxidation of Cycloalkanols by Sodium Nitrite with Molecular Oxygen in Trifluoroacetic Acid.

ChemInform ◽  
2005 ◽  
Vol 36 (5) ◽  
Author(s):  
Yoshihiro Matsumura ◽  
Yutaka Yamamoto ◽  
Noriaki Moriyama ◽  
Shigeru Furukubo ◽  
Fumiaki Iwasaki ◽  
...  
Keyword(s):  
Molecular Oxygen ◽  
Sodium Nitrite ◽  
Trifluoroacetic Acid
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