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Synthesis and Reactivity of 5‐Bromopenta‐2,4‐diynenitrile (BrC 5 N): an Access to π ‐Conjugated Scaffolds
Author(s) -
Kerisit Nicolas,
Ligny Romain,
Gauthier Etienne S.,
Guégan JeanPaul,
Toupet Loïc,
Guillemin JeanClaude,
Trolez Yann
Publication year - 2019
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201800232
Subject(s) - reactivity (psychology) , conjugated system , chemistry , amine gas treating , catalysis , combinatorial chemistry , palladium , organic chemistry , polymer chemistry , medicinal chemistry , polymer , medicine , alternative medicine , pathology
The synthesis of 5‐bromopenta‐2,4‐diynenitrile (BrC 5 N) in three steps from commercially available compounds is reported. Reacting 5‐bromopenta‐2,4‐diynenitrile with secondary amines led to the formation of stable butadiynamines or enynenitriles, depending on the nature of the amine reactant. The reaction of 5‐bromopenta‐2,4‐diynenitrile with simple terminal alkynes in the presence of secondary amines, copper, and palladium catalysts, provided a straightforward access to original polyfunctional carbon‐rich scaffolds. In this work, different alkynes and secondary amines were tested, which allowed for the preparation of a family of substituted dienes. Given the high synthetic potential of 5‐bromopenta‐2,4‐diynenitrile, we also prepared iodinated counterparts of this compound, that is, 5‐iodopenta‐2,4‐diynenitrile and its lower homologue 3‐iodopropiolonitrile. The UV‐visible spectrum of some relevant compounds was also recorded.