Synthesis and Reactivity of 5‐Bromopenta‐2,4‐diynenitrile (BrC5N): an Access to π‐Conjugated Scaffolds
The synthesis of 5‐bromopenta‐2,4‐diynenitrile (BrC5N) 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 rea...
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| Published in | Helvetica chimica acta Vol. 102; no. 3 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
01.03.2019
Wiley Subscription Services, Inc |
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| Online Access | Get full text |
| ISSN | 0018-019X 1522-2675 1522-2675 |
| DOI | 10.1002/hlca.201800232 |
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| Abstract | The synthesis of 5‐bromopenta‐2,4‐diynenitrile (BrC5N) 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. |
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| AbstractList | 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. The synthesis of 5‐bromopenta‐2,4‐diynenitrile (BrC5N) 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. 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. |
| ArticleNumber | 1800232 |
| Author | Gauthier, Etienne S. Kerisit, Nicolas Trolez, Yann Guégan, Jean‐Paul Ligny, Romain Toupet, Loïc Guillemin, Jean‐Claude |
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| Keywords | YNAMIDES CAPPED POLYYNES alkynes dienes ynamines TERMINAL ALKYNES POWERFUL enynes HALOGENO CYANO COMPOUNDS |
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| Snippet | The synthesis of 5‐bromopenta‐2,4‐diynenitrile (BrC5N) in three steps from commercially available compounds is reported. Reacting 5‐bromopenta‐2,4‐diynenitrile... The synthesis of 5‐bromopenta‐2,4‐diynenitrile (BrC 5 N) in three steps from commercially available compounds is reported. Reacting... The synthesis of 5-bromopenta-2,4-diynenitrile (BrC5N) in three steps from commercially available compounds is reported. Reacting 5-bromopenta-2,4-diynenitrile... The synthesis of 5-bromopenta-2,4-diynenitrile (BrC 5 N) in three steps from commercially available compounds is reported. Reacting... |
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| SubjectTerms | Alkynes Amines Catalysis Catalysts Chemical Sciences Chemistry Chemistry, Multidisciplinary Dienes enynes Homology Organic chemistry Palladium Physical Sciences Scaffolds Science & Technology Synthesis Visible spectrum ynamines |
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| Title | Synthesis and Reactivity of 5‐Bromopenta‐2,4‐diynenitrile (BrC5N): an Access to π‐Conjugated Scaffolds |
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