Metal-free aerobic oxidative C–N bond cleavage of tertiary amines for the synthesis of N-heterocycles with high atom efficiency

2014 ◽  
Vol 12 (23) ◽  
pp. 3802-3807 ◽  
Author(s):  
Xiuling Chen ◽  
Tieqiao Chen ◽  
Yongbo Zhou ◽  
Daoqing Han ◽  
Li-Biao Han ◽  
...  
Keyword(s):  
Molecular Oxygen ◽  
Bond Cleavage ◽  
Tertiary Amines ◽  
Metal Free ◽  
Alkyl Groups

An efficient metal-free aerobic C–N bond cleavage of tertiary amines has been developed to construct N-heterocycles using molecular oxygen as the sole oxidant with high atom efficiency. All of the three alkyl groups in tertiary amines can be utilized and transformed into N-heterocycles.

ChemInform Abstract: Metal-Free Aerobic Oxidative C-N Bond Cleavage of Tertiary Amines for the Synthesis of N-Heterocycles with High Atom Efficiency.

ChemInform ◽  
2014 ◽  
Vol 45 (44) ◽  
pp. no-no
Author(s):  
Xiuling Chen ◽  
Tieqiao Chen ◽  
Yongbo Zhou ◽  
Daoqing Han ◽  
Li-Biao Han ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Tertiary Amines ◽  
Metal Free

A metal-free and mild approach to 1,3,4-oxadiazol-2(3H)-ones via oxidative C–C bond cleavage using molecular oxygen

2018 ◽  
Vol 16 (12) ◽  
pp. 2105-2113 ◽  
Author(s):  
Bumhee Lim ◽  
Seunggun Park ◽  
Jae Hyun Park ◽  
Jongsik Gam ◽  
Sanghee Kim ◽  
...  
Keyword(s):  
Molecular Oxygen ◽  
Bond Cleavage ◽  
Cleavage Reaction ◽  
Metal Free ◽  
Bond Cleavage Reaction

A metal-free aerobic oxidative C–C bond cleavage reaction for the synthesis of 1,3,4-oxadiazol-2(3H)-ones is described.

Cu-catalyzed aerobic oxidative amidation of aryl alkyl ketones with azoles to afford tertiary amides via selective C–C bond cleavage

2015 ◽  
Vol 2 (7) ◽  
pp. 765-770 ◽  
Author(s):  
Wen Ding ◽  
Qiuling Song
Keyword(s):  
Molecular Oxygen ◽  
Bond Cleavage ◽  
Alkyl Groups ◽  
Aryl Ketones ◽  
Oxidative Amidation ◽  
Tertiary Amides ◽  
Long Chain

Chemoselective cleavage of the C(CO)–C(alkyl) bond in aryl ketones leading to azole amides is disclosed. Aryl ketones with a variety of long-chain alkyl groups have been demonstrated to be active substrates and mechanism studies suggested that molecular oxygen serves both as an oxidant and a reactant in this strategy.

Metal‐Free, Visible‐Light‐Induced Selective C−C Bond Cleavage of Cycloalkanones with Molecular Oxygen

2020 ◽  
Vol 26 (51) ◽  
pp. 11690-11694
Author(s):  
Hong Xin ◽  
Xin‐Hua Duan ◽  
Le Liu ◽  
Li‐Na Guo
Keyword(s):  
Visible Light ◽  
Molecular Oxygen ◽  
Bond Cleavage ◽  
Metal Free

Metal-Free Domino Oligocyclization Reactions of Enynals and Enynones with Molecular Oxygen

2021 ◽  
Vol 23 (4) ◽  
pp. 1291-1295
Author(s):  
Alireza Abbasi Kejani ◽  
Hormoz Khosravi ◽  
Frank Rominger ◽  
Saeed Balalaie ◽  
Bernhard Breit
Keyword(s):  
Molecular Oxygen ◽  
Metal Free

Visible-Light-Mediated Organoboron-Catalysed Metal-Free Dehydrogenation of N-Heterocycles Using Molecular Oxygen

2021 ◽  
Author(s):  
Lanfeng Wei ◽  
Yu Wei ◽  
Jinli Zhang ◽  
Liang Xu
Keyword(s):  
Visible Light ◽  
Molecular Oxygen ◽  
The Other ◽  
Metal Free ◽  
Other Hand

The surge of photocatalytic transformation not only provides unprecedented synthetical methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in...

scholarly journals Innentitelbild: Chemoselective Oxidative C(CO)C(methyl) Bond Cleavage of Methyl Ketones to Aldehydes Catalyzed by CuI with Molecular Oxygen (Angew. Chem. 43/2013)

2013 ◽  
Vol 125 (43) ◽  
pp. 11384-11384
Author(s):  
Lin Zhang ◽  
Xihe Bi ◽  
Xiaoxue Guan ◽  
Xingqi Li ◽  
Qun Liu ◽  
...  
Keyword(s):  
Molecular Oxygen ◽  
Bond Cleavage ◽  
Methyl Ketones

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.

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