A CO2-mediated conjugate cyanide addition to chalcones

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Standard

A CO2-mediated conjugate cyanide addition to chalcones. / Dotzauer, Simon; Hadaf, Gul Barg; Kamounah, Fadhil S.; Kadziola, Anders; Lee, Ji Woong.

I: Catalysts, Bind 10, Nr. 12, 1481, 12.2020, s. 1-9.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Dotzauer, S, Hadaf, GB, Kamounah, FS, Kadziola, A & Lee, JW 2020, 'A CO2-mediated conjugate cyanide addition to chalcones', Catalysts, bind 10, nr. 12, 1481, s. 1-9. https://doi.org/10.3390/catal10121481

APA

Dotzauer, S., Hadaf, G. B., Kamounah, F. S., Kadziola, A., & Lee, J. W. (2020). A CO2-mediated conjugate cyanide addition to chalcones. Catalysts, 10(12), 1-9. [1481]. https://doi.org/10.3390/catal10121481

Vancouver

Dotzauer S, Hadaf GB, Kamounah FS, Kadziola A, Lee JW. A CO2-mediated conjugate cyanide addition to chalcones. Catalysts. 2020 dec.;10(12):1-9. 1481. https://doi.org/10.3390/catal10121481

Author

Dotzauer, Simon ; Hadaf, Gul Barg ; Kamounah, Fadhil S. ; Kadziola, Anders ; Lee, Ji Woong. / A CO2-mediated conjugate cyanide addition to chalcones. I: Catalysts. 2020 ; Bind 10, Nr. 12. s. 1-9.

Bibtex

@article{55be02b31a104127a9f315206242ce0a,
title = "A CO2-mediated conjugate cyanide addition to chalcones",
abstract = "Carbon dioxide is an intrinsically stable molecule; however, it can readily react with various nucleophilic reagents. In the presence of a cyanide source, CO2 was proven to be useful to promote addition reactions. Here we report the use of CO2 to facilitate 1,4-conjugate cyanide addition reaction to chalcones to generate organonitriles. Nitriles are key component in organic synthesis due to their utility in numerous functional group transformation, however, conjugation addition of cyanide has been a challenge in this substrate class due to side reactions. To mitigate this, we employed simple ammonium and metal cyanide sources as nucleophiles under carbon dioxide atmosphere where high selectivity toward the desired product was obtained. The presented reaction is not feasible under inert atmosphere, which highlights the important role of CO2, as a Lewis and Br{\o}ndsted acidic catalyst. Further derivatization of organonitriles compounds were performed to showcase the utility of the reaction, while an unprecedented dimerization reaction was identified and characterized, affording a cyclopentanone scaffold.",
keywords = "Carbon dioxide, Catalysis, Cyanide, Heterocycles, Nitriles",
author = "Simon Dotzauer and Hadaf, {Gul Barg} and Kamounah, {Fadhil S.} and Anders Kadziola and Lee, {Ji Woong}",
year = "2020",
month = dec,
doi = "10.3390/catal10121481",
language = "English",
volume = "10",
pages = "1--9",
journal = "Catalysts",
issn = "2073-4344",
publisher = "M D P I AG",
number = "12",

}

RIS

TY - JOUR

T1 - A CO2-mediated conjugate cyanide addition to chalcones

AU - Dotzauer, Simon

AU - Hadaf, Gul Barg

AU - Kamounah, Fadhil S.

AU - Kadziola, Anders

AU - Lee, Ji Woong

PY - 2020/12

Y1 - 2020/12

N2 - Carbon dioxide is an intrinsically stable molecule; however, it can readily react with various nucleophilic reagents. In the presence of a cyanide source, CO2 was proven to be useful to promote addition reactions. Here we report the use of CO2 to facilitate 1,4-conjugate cyanide addition reaction to chalcones to generate organonitriles. Nitriles are key component in organic synthesis due to their utility in numerous functional group transformation, however, conjugation addition of cyanide has been a challenge in this substrate class due to side reactions. To mitigate this, we employed simple ammonium and metal cyanide sources as nucleophiles under carbon dioxide atmosphere where high selectivity toward the desired product was obtained. The presented reaction is not feasible under inert atmosphere, which highlights the important role of CO2, as a Lewis and Brøndsted acidic catalyst. Further derivatization of organonitriles compounds were performed to showcase the utility of the reaction, while an unprecedented dimerization reaction was identified and characterized, affording a cyclopentanone scaffold.

AB - Carbon dioxide is an intrinsically stable molecule; however, it can readily react with various nucleophilic reagents. In the presence of a cyanide source, CO2 was proven to be useful to promote addition reactions. Here we report the use of CO2 to facilitate 1,4-conjugate cyanide addition reaction to chalcones to generate organonitriles. Nitriles are key component in organic synthesis due to their utility in numerous functional group transformation, however, conjugation addition of cyanide has been a challenge in this substrate class due to side reactions. To mitigate this, we employed simple ammonium and metal cyanide sources as nucleophiles under carbon dioxide atmosphere where high selectivity toward the desired product was obtained. The presented reaction is not feasible under inert atmosphere, which highlights the important role of CO2, as a Lewis and Brøndsted acidic catalyst. Further derivatization of organonitriles compounds were performed to showcase the utility of the reaction, while an unprecedented dimerization reaction was identified and characterized, affording a cyclopentanone scaffold.

KW - Carbon dioxide

KW - Catalysis

KW - Cyanide

KW - Heterocycles

KW - Nitriles

U2 - 10.3390/catal10121481

DO - 10.3390/catal10121481

M3 - Journal article

AN - SCOPUS:85098190935

VL - 10

SP - 1

EP - 9

JO - Catalysts

JF - Catalysts

SN - 2073-4344

IS - 12

M1 - 1481

ER -

ID: 254722814