Latest Articles of European Journal of Organic Chemistry


New Facet of Azatriene Reactivity: A Short‐Cut to 5‐Amino‐3‐methyl‐4‐(1H‐pyrrol‐1‐yl)thiophene‐2‐carboxylates and 5‐Amino‐3‐methyl‐4‐(1H‐pyrrol‐1‐yl)thiophene‐2‐carbonitriles 10.1002/ejoc.201800268 2018-02-20 An expedient simple approach to highly functionalized tetrasubstituted thiophenes from readily accessible starting materials [(1H‐pyrrol‐1‐yl)allene, isothiocyanates, and alkyl 2‐bromoacetates or 2‐bromoacetonitrile] has been developed. The methodology is bas...
Cover Feature: Pre-Activation-Based Stereoselective Glycosylations (Eur. J. Org. Chem. /2018) 10.1002/ejoc.201800274 2018-02-20 The Cover Feature shows that pre-activation-based glycosylation separates donor activation and acceptor glycosylation into two distinct steps. As a result, unique stereochemical control can be achieved by judicious choices of protective groups, anomeric group...
Cover Feature: Nickel-Catalyzed Synthesis of Diaryl Sulfones from Aryl Halides and Sodium Sulfinates (Eur. J. Org. Chem. /2018) 10.1002/ejoc.201800174 2018-02-19 The Cover Feature shows the first nickel-catalyzed cross-coupling of sodium sulfinates with aryl bromides. This method enables a straightforward synthesis of diarylsulfones with high functional group compatibility. The active nickel-catalyst is generated in s...
Front Cover: Synthesis and Binding Studies of a Tetra-α Aryl-Extended Photoresponsive Calix[4]pyrrole Receptor Bearing meso-Alkyl Substituents (Eur. J. Org. Chem. /2018) 10.1002/ejoc.201800173 2018-02-19 The Front Cover shows two isomeric tetraazobenzene calix[4]pyrroles with a bound guest. The all-trans complex (lower left) is exclusively obtained after thermal equilibration. The biphenyl unit of the bound guest is fully included in the aromatic cavity of th...
Base‐mediated cyclization of 3‐[2‐(2‐oxo‐2‐phenylethyl)‐1‐pyrrolidinyl]propanenitrile to 7‐phenyl‐1,2,3,7,8,8a‐hexahydroindolizine‐6‐carbonitrile: what lies between? 10.1002/ejoc.201701714 2018-02-18 Three intermediates along the reaction path by which 3‐[2‐(2‐oxo‐2‐phenylethyl)‐1‐pyrrolidinyl]propanenitrile is converted into the rel‐(7R,8aR)‐ and (7R,8aS)‐diastereoisomers of 7‐phenyl‐1,2,3,7,8,8a‐hexahydroindolizine‐6‐carbonitrile upon treatment with pot...
Radical‐Induced, Palladium‐Catalyzed C‐H activation: A New Approach to Functionalize 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives with Toluenes, Aldehydes and Benzyl Alcohols 10.1002/ejoc.201800263 2018-02-17 In the present work, toluenes, aldehydes and benzyl alcohols have been exploited in the radical‐induced direct functionalization of heterocyclic molecules, in particular 4H‐benzo[d][1,3]oxazin‐4‐one derivatives via the palladium‐catalyzed C‐H activation strat...
Facile access to 12‐membered macrocyclic ligand PCTA and novel derivatives including carboxylate, amide and phosphinate ligating functionalities. 10.1002/ejoc.201800066 2018-02-16 We describe a convenient synthetic pathway for the access of the 12‐membered PCTA macrocycle, a polyaminocarboxylate ligand whose M2+ and M3+ complexes are commonly associated with applications in biomedical diagnostic and radiotherapy. The synthetic pathway ...
Naphthalene diimides prepared by straightforward method and its characterization for organic electronics 10.1002/ejoc.201701741 2018-02-16 A new approach in the synthesis of acetylene core substituted naphthalene diimides in polar solvent using PdCl2, Et3N and powder electrolytic copper was developed. This simplified approach allows for high‐throughput synthesis where the reaction products can b...
A Suzuki‐Miyaura Coupling of Ortho Hydroxy Aryl Bromide with Isopropenylboronic Pinacol Ester and its Application: Synthesis of the Potassium‐Channel Opener (+)‐Callitrisic Acid 10.1002/ejoc.201800070 2018-02-15 A Suzuki‐Miyaura coupling reaction of ortho hydroxy aromatic bromide 2 with isopropenylboronic acid pinacol ester has been investigated. It was found that the catalyst of Pd2(dba)3/PCy3 in dioxan‐water gave good yield by suppressing the isomerization of isopr...
Synthesis of 2‐acetylbenzonitriles and reactivity in tandem reactions with carbon‐ and hetero‐nucleophiles: easy access to 3,3‐disubstituted isoindolinones. 10.1002/ejoc.201800240 2018-02-15 The synthesis of 2‐acetylbenzonitriles has been conveniently achieved by oxidation of the respective 2‐ethylbenzonitriles, combining in one‐pot procedures radical bromination and hydrolysis reaction. The obtained ketones, reacted under very mild conditions wi...

New Facet of Azatriene Reactivity: A Short‐Cut to 5‐Amino‐3‐methyl‐4‐(1H‐pyrrol‐1‐yl)thiophene‐2‐carboxylates and 5‐Amino‐3‐methyl‐4‐(1H‐pyrrol‐1‐yl)thiophene‐2‐carbonitriles

10.1002/ejoc.201800268

2018-02-20

An expedient simple approach to highly functionalized tetrasubstituted thiophenes from readily accessible starting materials [(1H‐pyrrol‐1‐yl)allene, isothiocyanates, and alkyl 2‐bromoacetates or 2‐bromoacetonitrile] has been developed. The methodology is bas...

Cover Feature: Pre-Activation-Based Stereoselective Glycosylations (Eur. J. Org. Chem. /2018)

10.1002/ejoc.201800274

2018-02-20

The Cover Feature shows that pre-activation-based glycosylation separates donor activation and acceptor glycosylation into two distinct steps. As a result, unique stereochemical control can be achieved by judicious choices of protective groups, anomeric group...

Cover Feature: Nickel-Catalyzed Synthesis of Diaryl Sulfones from Aryl Halides and Sodium Sulfinates (Eur. J. Org. Chem. /2018)

10.1002/ejoc.201800174

2018-02-19

The Cover Feature shows the first nickel-catalyzed cross-coupling of sodium sulfinates with aryl bromides. This method enables a straightforward synthesis of diarylsulfones with high functional group compatibility. The active nickel-catalyst is generated in s...

Front Cover: Synthesis and Binding Studies of a Tetra-α Aryl-Extended Photoresponsive Calix[4]pyrrole Receptor Bearing meso-Alkyl Substituents (Eur. J. Org. Chem. /2018)

10.1002/ejoc.201800173

2018-02-19

The Front Cover shows two isomeric tetraazobenzene calix[4]pyrroles with a bound guest. The all-trans complex (lower left) is exclusively obtained after thermal equilibration. The biphenyl unit of the bound guest is fully included in the aromatic cavity of th...

Base‐mediated cyclization of 3‐[2‐(2‐oxo‐2‐phenylethyl)‐1‐pyrrolidinyl]propanenitrile to 7‐phenyl‐1,2,3,7,8,8a‐hexahydroindolizine‐6‐carbonitrile: what lies between?

10.1002/ejoc.201701714

2018-02-18

Three intermediates along the reaction path by which 3‐[2‐(2‐oxo‐2‐phenylethyl)‐1‐pyrrolidinyl]propanenitrile is converted into the rel‐(7R,8aR)‐ and (7R,8aS)‐diastereoisomers of 7‐phenyl‐1,2,3,7,8,8a‐hexahydroindolizine‐6‐carbonitrile upon treatment with pot...

Radical‐Induced, Palladium‐Catalyzed C‐H activation: A New Approach to Functionalize 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives with Toluenes, Aldehydes and Benzyl Alcohols

10.1002/ejoc.201800263

2018-02-17

In the present work, toluenes, aldehydes and benzyl alcohols have been exploited in the radical‐induced direct functionalization of heterocyclic molecules, in particular 4H‐benzo[d][1,3]oxazin‐4‐one derivatives via the palladium‐catalyzed C‐H activation strat...

Facile access to 12‐membered macrocyclic ligand PCTA and novel derivatives including carboxylate, amide and phosphinate ligating functionalities.

10.1002/ejoc.201800066

2018-02-16

We describe a convenient synthetic pathway for the access of the 12‐membered PCTA macrocycle, a polyaminocarboxylate ligand whose M2+ and M3+ complexes are commonly associated with applications in biomedical diagnostic and radiotherapy. The synthetic pathway ...

Naphthalene diimides prepared by straightforward method and its characterization for organic electronics

10.1002/ejoc.201701741

2018-02-16

A new approach in the synthesis of acetylene core substituted naphthalene diimides in polar solvent using PdCl2, Et3N and powder electrolytic copper was developed. This simplified approach allows for high‐throughput synthesis where the reaction products can b...

A Suzuki‐Miyaura Coupling of Ortho Hydroxy Aryl Bromide with Isopropenylboronic Pinacol Ester and its Application: Synthesis of the Potassium‐Channel Opener (+)‐Callitrisic Acid

10.1002/ejoc.201800070

2018-02-15

A Suzuki‐Miyaura coupling reaction of ortho hydroxy aromatic bromide 2 with isopropenylboronic acid pinacol ester has been investigated. It was found that the catalyst of Pd2(dba)3/PCy3 in dioxan‐water gave good yield by suppressing the isomerization of isopr...

Synthesis of 2‐acetylbenzonitriles and reactivity in tandem reactions with carbon‐ and hetero‐nucleophiles: easy access to 3,3‐disubstituted isoindolinones.

10.1002/ejoc.201800240

2018-02-15

The synthesis of 2‐acetylbenzonitriles has been conveniently achieved by oxidation of the respective 2‐ethylbenzonitriles, combining in one‐pot procedures radical bromination and hydrolysis reaction. The obtained ketones, reacted under very mild conditions wi...