Regioselective <i>ortho</i>‐Palladation of [2.2]Paracyclophane Scaffolds: Accessing Planar and Central Chiral N,C‐Palladacycles

Zippel, Christoph; Bartholomeyzik, Teresa; Friedmann, Christian; Nieger, Martin; Hassan, Zahid; Bräse, Stefan

doi:10.1002/ejoc.202101066

Cited by 6 publications

(2 citation statements)

References 48 publications

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“…[19] We have reported PCP-based planar and central chiral N,C-palladacycles by regioselective ortho-palladation of amine-and iminefunctionalized PCPs. [20] To showcase the utilization of the obtained cyclophanyl imidazole ligands, we applied this orthopalladation method, employing stepwise Pd(OAc) 2 and LiCl followed by subsequent treatment with PPh 3 (Scheme 5). N,Cpalladacycle 16 was obtained in 37 % yield in a highly selective manner.…”

Section: Cyclophanyl Imidazole Ligands For Nc-palladacyclesmentioning

confidence: 99%

Cover Feature: Diversity‐Oriented Synthesis of [2.2]Paracyclophane‐derived Fused Imidazo[1,2‐a]heterocycles by Groebke‐Blackburn‐Bienaymé Reaction: Accessing Cyclophanyl Imidazole Ligands Library (Chem. Eur. J. 3/2022)

Stahlberger

Schwarz

Zippel

et al. 2021

Chemistry A European J

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The Groebke–Blackburn–Bienaymé three‐component reaction (GBB‐3CR) has contributed enormously to the progress of organic synthesis, medicinal chemistry, and materials science. Diversity‐oriented synthesis of skeletally diverse cyclophanyl‐derived fused imidazo[1,2‐a]heterocycles by one‐pot GBB‐3CR involving formyl‐cyclophane components in combination with various aliphatic and aromatic isocyanides and heteroaromatic amidines gives a library of versatile cyclophanyl imidazoles ligands. These can be readily transformed to prepare N,C palladacycles by regioselective ortho‐palladation. More information can be found in the Full Paper by S. Bräse et al. (DOI: 10.1002/chem.202103511).

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Section: Cyclophanyl Imidazole Ligands For Nc-palladacyclesmentioning

confidence: 99%

Cover Feature: Diversity‐Oriented Synthesis of [2.2]Paracyclophane‐derived Fused Imidazo[1,2‐a]heterocycles by Groebke‐Blackburn‐Bienaymé Reaction: Accessing Cyclophanyl Imidazole Ligands Library (Chem. Eur. J. 3/2022)

Stahlberger

Schwarz

Zippel

et al. 2021

Chemistry A European J

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show abstract

“…[19] We have reported PCP‐based planar and central chiral N,C‐palladacycles by regioselective ortho ‐palladation of amine‐ and imine‐functionalized PCPs. [20] To showcase the utilization of the obtained cyclophanyl imidazole ligands, we applied this ortho ‐palladation method, employing stepwise Pd(OAc) 2 and LiCl followed by subsequent treatment with PPh 3 (Scheme 5 ). N,C‐palladacycle 16 was obtained in 37 % yield in a highly selective manner.…”

Section: Cyclophanyl Imidazole Ligands For Nc‐palladacyclesmentioning

confidence: 99%

Diversity‐Oriented Synthesis of [2.2]Paracyclophane‐derived Fused Imidazo[1,2‐a]heterocycles by Groebke‐Blackburn‐Bienaymé Reaction: Accessing Cyclophanyl Imidazole Ligands Library

Stahlberger

Schwarz

Hassan

et al. 2021

Chemistry A European J

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This report describes the synthesis of a [2.2]paracyclophane-derived annulated 3-amino-imidazole ligand library through a Groebke-Blackburn-Bienaymé threecomponent reaction (GBB-3CR) approach employing formylcyclophanes in combination with diverse aliphatic and aromatic isocyanides and heteroaromatic amidines. The GBB-3CR process gives access to skeletally-diverse cyclophanyl imidazole ligands, namely 3-amino-imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrazines. Additionally, a one-pot protocol [a

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Design Strategies for Structurally Controlled Polymer Surfaces via Cyclophane‐Based CVD Polymerization and Post‐CVD Fabrication

et al. 2022

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Molecular structuring of soft matter with precise arrangements over multiple hierarchical levels, especially on polymer surfaces, and enabling their post‐synthetic modulation has tremendous potential for application in molecular engineering and interfacial science. Here, recent research and developments in design strategies for structurally controlled polymer surfaces via cyclophane‐based chemical vapor deposition (CVD) polymerization with precise control over chemical functionalities and post‐CVD fabrication via orthogonal surface functionalization that facilitates the formation of designable biointerfaces are summarized. Particular discussion about innovative approaches for the templated synthesis of shape‐controlled CVD polymers, ranging from 1D to 3D architecture, including inside confined nanochannels, nanofibers/nanowires synthesis into an anisotropic media such as liquid crystals, and CVD polymer nanohelices via hierarchical chirality transfer across multiple length scales is provided. Aiming at multifunctional polymer surfaces via CVD copolymerization of multiple precursors, the structural and functional design of the fundamental [2.2]paracyclophane (PCP) precursor molecules, that is, functional CVD monomer chemistry is also described. Technologically advanced and innovative surface deposition techniques toward topological micro‐ and nanostructuring, including microcontact printing, photopatterning, photomask, and lithographic techniques such as dip‐pen nanolithography, showcasing research from the authors’ laboratories as well as other's relevant important findings in this evolving field are highlighted that have introduced new programmable CVD polymerization capabilities. Perspectives, current limitations, and future considerations are provided.

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Regioselective ortho‐Palladation of [2.2]Paracyclophane Scaffolds: Accessing Planar and Central Chiral N,C‐Palladacycles

Abstract: Figure 1. Representative previous work on non-cyclophanyl and cyclophanyl-derived cyclometallated complexes.

Cited by 6 publications

References 48 publications

Cover Feature: Diversity‐Oriented Synthesis of [2.2]Paracyclophane‐derived Fused Imidazo[1,2‐a]heterocycles by Groebke‐Blackburn‐Bienaymé Reaction: Accessing Cyclophanyl Imidazole Ligands Library (Chem. Eur. J. 3/2022)

Cover Feature: Diversity‐Oriented Synthesis of [2.2]Paracyclophane‐derived Fused Imidazo[1,2‐a]heterocycles by Groebke‐Blackburn‐Bienaymé Reaction: Accessing Cyclophanyl Imidazole Ligands Library (Chem. Eur. J. 3/2022)

Diversity‐Oriented Synthesis of [2.2]Paracyclophane‐derived Fused Imidazo[1,2‐a]heterocycles by Groebke‐Blackburn‐Bienaymé Reaction: Accessing Cyclophanyl Imidazole Ligands Library

Design Strategies for Structurally Controlled Polymer Surfaces via Cyclophane‐Based CVD Polymerization and Post‐CVD Fabrication

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