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Pd‐Catalyzed Coupling of Non‐Activated Dibromoarenes to 2,3‐Diaminoarenes: Formation of N , N ′‐Dihydropyrazines
Author(s) -
Engelhart Jens U.,
Lindner Benjamin D.,
Tverskoy Olena,
Rominger Frank,
Bunz Uwe H. F.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303277
Subject(s) - catalysis , product (mathematics) , coupling (piping) , service (business) , chemistry , computer science , combinatorial chemistry , information retrieval , organic chemistry , business , materials science , mathematics , marketing , metallurgy , geometry
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.