Pd-Catalyzed Coupling of Non-Activated Dibromoarenes to 2,3-Diaminoarenes: Formation of N,N′-Dihydropyrazines

Accessible azaacenes: Pd‐catalyzed coupling reactions between aromatic diamines and unactivated aromatic dibromides furnish N,N′‐dihydrodiazapentacenes, ‐hexacenes, and ‐heptacenes (see scheme; TIPS=triisopropylsilyl). Oxidation of these products led to diazapentacenes and a diazahexacene. The exist...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2013-11, Vol.19 (45), p.15089-15092
Main Authors: Engelhart, Jens U., Lindner, Benjamin D., Tverskoy, Olena, Rominger, Frank, Bunz, Uwe H. F.
Format: Article
Language:English
Subjects:
Accessibility
alkynes
azapentacenes
Chemical reactions
Chemistry
Diamines
Dibromides
Dimerization
Formations
heteroacenes
Joining
Palladium
palladium catalysis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Accessible azaacenes: Pd‐catalyzed coupling reactions between aromatic diamines and unactivated aromatic dibromides furnish N,N′‐dihydrodiazapentacenes, ‐hexacenes, and ‐heptacenes (see scheme; TIPS=triisopropylsilyl). Oxidation of these products led to diazapentacenes and a diazahexacene. The existence of a diazaheptacene intermediate was proven by solving the single‐crystal structure of its (4+4) dimerization product.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201303277