Triflate-functionalized calix[6]arenes as versatile building-blocks: application to the synthesis of an inherently chiral Zn(ii) complex

2016 ◽  
Vol 14 (6) ◽  
pp. 1950-1957 ◽  
Author(s):  
Sara Zahim ◽  
Roy Lavendomme ◽  
Olivia Reinaud ◽  
Michel Luhmer ◽  
Gwilherm Evano ◽  
...  
Keyword(s):  
Building Blocks ◽  
Regioselective Synthesis ◽  
Inherently Chiral

The regioselective synthesis of two calix[6]arenes bearing triflate groups is described. These compounds constitute versatile molecular platforms that allow the elaboration of sophisticated calixarene-based systems selectively functionalized at the large and/or at the small rim.

scholarly journals Practical and Regioselective Synthesis of C4-Alkylated Pyridines

2021 ◽  
Author(s):  
jin choi ◽  
Gabriele Laudadio ◽  
Edouard Godineau ◽  
Phil Baran
Keyword(s):  
Carboxylic Acid ◽  
Late Stage ◽  
Building Blocks ◽  
Regioselective Synthesis ◽  
Heterocyclic Chemistry ◽  
Blocking Group ◽  
Functionalized Materials

The direct position-selective C–4 alkylation of pyridines has been a longstanding challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using pre-functionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C–4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple, scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci as a late-stage functionalization technique.

scholarly journals Triptycene Derivatives: From Their Synthesis to Their Unique Properties

Molecules ◽  
2021 ◽  
Vol 27 (1) ◽  
pp. 250
Author(s):  
Mateusz Woźny ◽  
Adam Mames ◽  
Tomasz Ratajczyk
Keyword(s):  
Molecular Interactions ◽  
Building Blocks ◽  
Regioselective Synthesis ◽  
Molecular Scaffolds ◽  
Synthetic Methodology ◽  
New Developments ◽  
Solid States ◽  
New Approaches ◽  
Sterically Demanding ◽  
Great Progress

Since the first preparation of triptycene, great progress has been made with respect to its synthesis and the understanding of its properties. Interest in triptycene-based systems is intense; in recent years, advances in the synthetic methodology and properties of new triptycenes have been reported by researchers from various fields of science. Here, an account of these new developments is given and placed in reference to earlier pivotal works that underpin the field. First, we discuss new approaches to the synthesis of new triptycenes. Progress in the regioselective synthesis of sterically demanding systems is discussed. The application of triptycenes in catalysis is also presented. Next, progress in the understanding of the relations between triptycene structures and their properties is discussed. The unique properties of triptycenes in the liquid and solid states are elaborated. Unique interactions, which involve triptycene molecular scaffolds, are presented. Molecular interactions within a triptycene unit, as well as between triptycenes or triptycenes and other molecules, are also evaluated. In particular, the summary of the synthesis and useful features will be helpful to researchers who are using triptycenes as building blocks in the chemical and materials sciences.

4-Chloro-3-(trifluoroacetyl)- and 4-chloro-3-(methoxalyl)coumarins as novel and efficient building blocks for the regioselective synthesis of 3,4-fused coumarins

Tetrahedron ◽  
2011 ◽  
Vol 67 (41) ◽  
pp. 7946-7955 ◽  
Author(s):  
Viktor O. Iaroshenko ◽  
Friedrich Erben ◽  
Satenik Mkrtchyan ◽  
Ani Hakobyan ◽  
Marcelo Vilches-Herrera ◽  
...  
Keyword(s):  
Building Blocks ◽  
Regioselective Synthesis

An expeditious regioselective synthesis of [60]fullerene e,e,e tris-adduct building blocks

2013 ◽  
Vol 54 (32) ◽  
pp. 4241-4244 ◽  
Author(s):  
David Sigwalt ◽  
Franck Schillinger ◽  
Sebastiano Guerra ◽  
Michel Holler ◽  
Mathilde Berville ◽  
...  
Keyword(s):  
Building Blocks ◽  
Regioselective Synthesis

scholarly journals Practical and Regioselective Synthesis of C4-Alkylated Pyridines

2021 ◽  
Author(s):  
jin choi ◽  
Gabriele Laudadio ◽  
Edouard Godineau ◽  
Phil Baran
Keyword(s):  
Carboxylic Acid ◽  
Late Stage ◽  
Building Blocks ◽  
Regioselective Synthesis ◽  
Heterocyclic Chemistry ◽  
Blocking Group ◽  
Functionalized Materials

The direct position-selective C–4 alkylation of pyridines has been a longstanding challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using pre-functionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C–4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple, scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci as a late-stage functionalization technique.

scholarly journals Surface engineering of a Cu-based heterogeneous catalyst for efficient azide-alkyne click cycloaddition

2021 ◽  
Author(s):  
Gianvito Vilé ◽  
Jiaxu Liu ◽  
Zhenmei Zhang
Keyword(s):  
Heterogeneous Catalyst ◽  
Active Site ◽  
Surface Engineering ◽  
Building Blocks ◽  
Atomic Scale ◽  
Regioselective Synthesis

In this work, we disclose that atomic-scale engineering of the active site in copper-based catalysts can effectively tune the material performance for the regioselective synthesis of triazoles, important building blocks...

scholarly journals Practical and Regioselective Synthesis of C4-Alkylated Pyridines

2021 ◽  
Author(s):  
jin choi ◽  
Gabriele Laudadio ◽  
Edouard Godineau ◽  
Phil Baran
Keyword(s):  
Carboxylic Acid ◽  
Late Stage ◽  
Building Blocks ◽  
Regioselective Synthesis ◽  
Heterocyclic Chemistry ◽  
Blocking Group ◽  
Functionalized Materials

The direct position-selective C–4 alkylation of pyridines has been a longstanding challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using pre-functionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C–4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple, scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci as a late-stage functionalization technique.

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