scholarly journals Ester Dance Reaction on the Aromatic Ring

2019 ◽  
Author(s):  
Kaoru Matsushita ◽  
Ryosuke Takise ◽  
Kei Muto ◽  
Junichiro Yamaguchi
Keyword(s):  
Carbon Atom ◽  
Aromatic Ring ◽  
Functional Group ◽  
State Of The Art ◽  
Palladium Catalysis ◽  
Ester Group ◽  
Halogen Atoms ◽  
Ester Moiety ◽  
Rearrangement Reactions ◽  
Halogen Dance Reaction

Aromatic rearrangement reactions are useful tools in the organic chemist’s toolbox when generating uncommon substitution patterns. However, it is difficult to precisely translocate a functional group in (hetero)arene systems, with the exception of halogen atoms in a halogen dance reaction. Herein, we describe an unprecedented “ester dance” reaction: a predictable translocation of an ester group from one carbon atom to another on an aromatic ring. Specifically, a phenyl carboxylate substituent can be shifted from one carbon to an adjacent carbon on a (hetero)aromatic ring under palladium catalysis to often give a thermodynamically favored, regioisomeric product with modest to good conversions. The obtained ester moiety can be further converted to various aromatic derivatives through the use of classic as well as state-of-the-art transformations including an amidation, acylations and decarbonylative couplings.

scholarly journals Ester dance reaction on the aromatic ring

2020 ◽  
Vol 6 (28) ◽  
pp. eaba7614
Author(s):  
Kaoru Matsushita ◽  
Ryosuke Takise ◽  
Kei Muto ◽  
Junichiro Yamaguchi
Keyword(s):  
Carbon Atom ◽  
Aromatic Ring ◽  
Functional Group ◽  
State Of The Art ◽  
Palladium Catalysis ◽  
Ester Group ◽  
Halogen Atoms ◽  
Ester Moiety ◽  
Rearrangement Reactions ◽  
Halogen Dance Reaction

Aromatic rearrangement reactions are useful tools in the organic chemist’s toolbox when generating uncommon substitution patterns. However, it is difficult to precisely translocate a functional group in (hetero) arene systems, with the exception of halogen atoms in a halogen dance reaction. Here, we describe an unprecedented “ester dance” reaction: a predictable translocation of an ester group from one carbon atom to another on an aromatic ring. Specifically, a phenyl carboxylate substituent can be shifted from one carbon to an adjacent carbon on a (hetero) aromatic ring under palladium catalysis to often give a thermodynamically favored, regioisomeric product with modest to good conversions. The obtained ester moiety can be further converted to various aromatic derivatives through the use of classic and state-of-the-art transformations including amidation, acylations, and decarbonylative couplings.

scholarly journals Ester Dance Reaction on the Aromatic Ring

2019 ◽  
Author(s):  
Kaoru Matsushita ◽  
Ryosuke Takise ◽  
Kei Muto ◽  
Junichiro Yamaguchi
Keyword(s):  
Carbon Atom ◽  
Aromatic Ring ◽  
Functional Group ◽  
State Of The Art ◽  
Palladium Catalysis ◽  
Ester Group ◽  
Halogen Atoms ◽  
Ester Moiety ◽  
Rearrangement Reactions ◽  
Halogen Dance Reaction

Aromatic rearrangement reactions are useful tools in the organic chemist’s toolbox when generating uncommon substitution patterns. However, it is difficult to precisely translocate a functional group in (hetero)arene systems, with the exception of halogen atoms in a halogen dance reaction. Herein, we describe an unprecedented “ester dance” reaction: a predictable translocation of an ester group from one carbon atom to another on an aromatic ring. Specifically, a phenyl carboxylate substituent can be shifted from one carbon to an adjacent carbon on a (hetero)aromatic ring under palladium catalysis to often give a thermodynamically favored, regioisomeric product with modest to good conversions. The obtained ester moiety can be further converted to various aromatic derivatives through the use of classic as well as state-of-the-art transformations including an amidation, acylations and decarbonylative couplings.

A Domino Heck Coupling–Cyclization–Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines

Synthesis ◽  
2021 ◽  
Author(s):  
Santanu Ghora ◽  
Chinnabattigalla Sreenivasulu ◽  
Gedu Satyanarayana
Keyword(s):  
Functional Group ◽  
Exchange Process ◽  
Palladium Catalysis ◽  
Allylic Alcohols ◽  
Heck Coupling ◽  
One Pot ◽  
Synthetic Process ◽  
Intramolecular Condensation ◽  
The One

AbstractAn efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence. Notably, this protocol occurs in water as a green solvent. Significantly, the method exhibits broad substrate scope and is applied for the synthesis of deuterated quinolines through a deuterium-exchange process.

scholarly journals Methyl 4-(bromomethyl)benzoate

2007 ◽  
Vol 63 (3) ◽  
pp. o1334-o1335 ◽  
Author(s):  
H. S. Yathirajan ◽  
S. Bindya ◽  
B. K. Sarojini ◽  
B. Narayana ◽  
Michael Bolte
Keyword(s):  
Aromatic Ring ◽  
Title Compound ◽  
Ester Group ◽  
Geometric Parameters ◽  
Compound C

The ester group of the title compound, C9H9BrO2, is only slightly twisted out of the plane of the central aromatic ring. Geometric parameters are in the usual ranges.

scholarly journals Methyl 3,5-bis(cyclohexylmethoxy)benzoate

2014 ◽  
Vol 70 (4) ◽  
pp. o400-o401 ◽  
Author(s):  
Peter W. R. Corfield ◽  
Michele L. Paccagnini ◽  
Amy M. Balija
Keyword(s):  
Methyl Ester ◽  
Hydrogen Bonds ◽  
Aromatic Ring ◽  
Title Compound ◽  
Ester Group ◽  
Interplanar Distance ◽  
Compound C ◽  
The Mean

In the title compound, C22H32O4, the atoms of the methyl ester group and the alkoxy O atoms are all coplanar with the central aromatic ring, with an r.m.s. deviation of 0.008 Å. Bonds to the methylene and cyclohexyl groups are also very close to this plane, so that the molecule is essentially flat, apart from the cyclohexyl groups. The mean planes through the cyclohexyl groups are tilted by 30.08 (9) and 36.14 (7)° with respect to the central aromatic ring. In the crystal, pairs of molecules linked by C—H...O hydrogen bonds form planar units which are stacked along theaaxis, with an average interplanar distance of 3.549 (2) Å. Stacking appears to be stabilized by further weak C—H...O hydrogen bonds.

Remarkably Slow Rotation about a Single Bond between an sp3-Hybridised Carbon Atom and an Aromatic Ring withoutorthoSubstituents

2009 ◽  
Vol 15 (9) ◽  
pp. 2185-2189 ◽  
Author(s):  
Sarah Murrison ◽  
David Glowacki ◽  
Christian Einzinger ◽  
James Titchmarsh ◽  
Stephen Bartlett ◽  
...  
Keyword(s):  
Carbon Atom ◽  
Aromatic Ring ◽  
Slow Rotation ◽  
Single Bond

The Encephalopathic Action of Five-carbon-atom Fatty Acids in the Rabbit

1976 ◽  
Vol 50 (6) ◽  
pp. 463-472 ◽  
Author(s):  
P. F. Teychenne ◽  
I. Walters ◽  
L. E. Claveria ◽  
D. B. Calne ◽  
Jane Price ◽  
...  
Keyword(s):  
Carbon Atom ◽  
Functional Group ◽  
Low Frequency ◽  
Isovaleric Acid ◽  
Valeric Acid ◽  
Inborn Errors ◽  
Pronounced Increase ◽  
Tiglic Acid ◽  
Ventriculocisternal Perfusion ◽  
Electroencephalographic Recording

1. Five-carbon-atom organic acids (C-5 acids) have been administered intravenously to rabbits with ventriculocisternal perfusion and continuous electroencephalographic recording (EEG). The concentration of the acids in the cerebrospinal fluid (CSF) perfusate have been compared with changes in integrated low-frequency activity in the EEG. 2. The C-5 acids investigated were those accumulating in inborn errors of metabolism, i.e. isovaleric acid, β-methylcrotonic acid, tiglic acid and α-keto- and α-hydroxy-isovaleric acid. Their activity was compared with that of valeric acid. 3. Valeric acid and isovaleric acid produced coma and pronounced increase in slow-wave electrical activity and these changes paralleled the increase in concentration of the acids in the CSF perfusate. 4. The concentration of β-methylcrotonic acid and tiglic acid in the CSF perfusate reached values comparable with valeric acid and isovaleric acid but showed less encephalopathic activity. An interaction between β-methylcrotonic acid and isovaleric acid was observed. 5. Although the concentrations of α-ketoisovaleric acid and α-hydroxyisovaleric acid rose to the lesser extent in the CSF perfusate, changes in reusability of the animal and in the EEG recording were demonstrated. 6. It is concluded that all the C-5 acids tested have encephalopathic activity although this is lessened by the presence of either a double bond or an oxygenated functional group.

Asymmetric hydrogenation via architectural and functional molecular engineering

2001 ◽  
Vol 73 (2) ◽  
pp. 227-232 ◽  
Author(s):  
Ryoji Noyori ◽  
Masatoshi Koizumi ◽  
Dai Ishii ◽  
Takeshi Ohkuma
Keyword(s):  
Asymmetric Synthesis ◽  
Nitro Group ◽  
Functional Group ◽  
Asymmetric Hydrogenation ◽  
Molecular Engineering ◽  
The Novel ◽  
Bifunctional Mechanism ◽  
Chiral Compounds ◽  
Halogen Atoms ◽  
Metal Ligand

RuCl2 (phosphine) 2 (1,2-diamine) complexes, coupled with an alkaline base in 2-propanol, allows for preferential hydrogenation of a C=O function over coexisting conjugated or nonconjugated C=C linkages, a nitro group, halogen atoms, and various heterocycles. The functional group selectivity is based on the novel metal-ligand bifunctional mechanism. The use of appropriate chiral diphosphines and diamines results in rapid and productive asymmetric hydrogenation of a range of aromatic, hetero-aromatic, and olefinic ketones. The versatility of this method is manifested by the asymmetric synthesis of various biologically significant chiral compounds.

scholarly journals Methylidynetrisphosphonates: Promising C1building block for the design of phosphate mimetics

2013 ◽  
Vol 9 ◽  
pp. 991-1001 ◽  
Author(s):  
Vadim D Romanenko ◽  
Valery P Kukhar
Keyword(s):  
Carbon Atom ◽  
Metal Ions ◽  
Building Block ◽  
State Of The Art ◽  
The State ◽  
Backbone Structure ◽  
Endogenous Metabolites

Methylidynetrisphosphonates are representatives of geminal polyphosphonates bearing three phosphonate (PO3H2) groups at the bridged carbon atom. Like well-known methylenebisphosphonates (BPs), they are characterized by a P–C–P backbone structure and are chemically stable mimetics of the endogenous metabolites, i.e., inorganic pyrophosphates (PPi). Because of its analogy to PPiand an ability to chelate metal ions, the 1,1,1-trisphosphonate structure is of great potential as a C1building block for the design of phosphate mimetics. The purpose of this review is to present a concise summary of the state of the art in trisphosphonate chemistry with particular emphasis on the synthesis, structure, reactions, and potential medicinal applications of these compounds.

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