Synthesis, electrochemical and spectroscopic studies of highly extended tetraaryl-m-phenylenediamines as precursors of ground-state triplet dications

An efficient protocol for the palladium‐catalyzed synthesis of sterically congested triarylamines from commercially available 1‐chloro‐ or 1‐bromonaphthalenes and diarylamines is described. The application of alkyllithium reagents as strong bases and a combination of Pd(OAc)2 and SPhos (2‐dicyclohexylphosphino‐2′,6′‐dimethoxybiphenyl) plays a crucial role in the success of this otherwise difficult to achieve C–N coupling reaction. A variety of secondary aromatic amines with versatile steric and electronic properties can be successfully used in this transformation to give the desired triarylamines in up to 99 % yield. The obtained products are important structural motifs in hole‐transport materials for organic light‐emitting diode applications.

show abstract

Synthesis of Sterically Congested Triarylamines by Palladium‐Catalyzed Amination

Riedmüller¹,

Kaufhold²,

Spreitzer³

et al. 2014

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Organic high-spin systems: Synthesis, electrochemical and spectroscopic studies of π-extended tetraaryl m-phenylenediamines

et al. 2009

View full text Add to dashboard Cite

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Synthesis, electrochemical and spectroscopic studies of highly extended tetraaryl-m-phenylenediamines as precursors of ground-state triplet dications

Cited by 2 publications

References 16 publications

Synthesis of Sterically Congested Triarylamines by Palladium‐Catalyzed Amination

Synthesis of Sterically Congested Triarylamines by Palladium‐Catalyzed Amination

Organic high-spin systems: Synthesis, electrochemical and spectroscopic studies of π-extended tetraaryl m-phenylenediamines

Contact Info

Product

Resources

About