The <i>hetero</i>-Friedel-Crafts-Bradsher Cyclizations with Formation of Ring Carbon-Heteroatom (P, S) Bonds, Leading to Organic Functional Materials
The interest in functional materials possessing improved properties led to development of new methods of their synthesis, which allowed to obtain new molecular arrangements with carbon and heteroatom motifs. Two of the classical reactions of versatile use are the Friedel-Crafts and the Bradsher reac...
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MDPI AG
2020-10-01
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| Series: | Materials |
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| Online Access: | https://www.mdpi.com/1996-1944/13/21/4751 |
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| author | Joanna Skalik Marek Koprowski Ewa Różycka-Sokołowska Piotr Bałczewski |
| author_facet | Joanna Skalik Marek Koprowski Ewa Różycka-Sokołowska Piotr Bałczewski |
| author_sort | Joanna Skalik |
| collection | DOAJ |
| description | The interest in functional materials possessing improved properties led to development of new methods of their synthesis, which allowed to obtain new molecular arrangements with carbon and heteroatom motifs. Two of the classical reactions of versatile use are the Friedel-Crafts and the Bradsher reactions, which in the new heteroatomic versions allow to replace ring carbon atoms by heteroatoms. In the present work, we review methods of synthesis of C–S and C–P bonds utilizing <i>thia</i>- and <i>phospha</i>-Friedel-Crafts-Bradsher cyclizations. Single examples of C–As and lack of C–Se bond formation, involving two of the closest neighbors of P and S in the periodic table, have also been noted. Applications of the obtained π-conjugated molecules, mainly as semiconducting materials, flame retardants, and resins hardeners, designed on the basis of five- and six-membered cyclic molecules containing ring phosphorus and sulfur atoms, are also included. This comprehensive review covers literature up to August 2020. |
| first_indexed | 2024-03-10T15:22:46Z |
| format | Article |
| id | doaj.art-84dca7186b904219a3b12570998904e6 |
| institution | Directory Open Access Journal |
| issn | 1996-1944 |
| language | English |
| last_indexed | 2024-03-10T15:22:46Z |
| publishDate | 2020-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Materials |
| spelling | doaj.art-84dca7186b904219a3b12570998904e62023-11-20T18:21:20ZengMDPI AGMaterials1996-19442020-10-011321475110.3390/ma13214751The <i>hetero</i>-Friedel-Crafts-Bradsher Cyclizations with Formation of Ring Carbon-Heteroatom (P, S) Bonds, Leading to Organic Functional MaterialsJoanna Skalik0Marek Koprowski1Ewa Różycka-Sokołowska2Piotr Bałczewski3Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, PolandDivision of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, PolandInstitute of Chemistry, Faculty of Science and Technology, Jan Długosz University in Częstochowa, Armii Krajowej 13/15, 42-201 Częstochowa, PolandDivision of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, PolandThe interest in functional materials possessing improved properties led to development of new methods of their synthesis, which allowed to obtain new molecular arrangements with carbon and heteroatom motifs. Two of the classical reactions of versatile use are the Friedel-Crafts and the Bradsher reactions, which in the new heteroatomic versions allow to replace ring carbon atoms by heteroatoms. In the present work, we review methods of synthesis of C–S and C–P bonds utilizing <i>thia</i>- and <i>phospha</i>-Friedel-Crafts-Bradsher cyclizations. Single examples of C–As and lack of C–Se bond formation, involving two of the closest neighbors of P and S in the periodic table, have also been noted. Applications of the obtained π-conjugated molecules, mainly as semiconducting materials, flame retardants, and resins hardeners, designed on the basis of five- and six-membered cyclic molecules containing ring phosphorus and sulfur atoms, are also included. This comprehensive review covers literature up to August 2020.https://www.mdpi.com/1996-1944/13/21/4751sulfurphosphorussulfoxide<i>thia</i>-Friedel-Crafts-Bradsher<i>phospha</i>-Friedel-Crafts-Bradshercyclization |
| spellingShingle | Joanna Skalik Marek Koprowski Ewa Różycka-Sokołowska Piotr Bałczewski The <i>hetero</i>-Friedel-Crafts-Bradsher Cyclizations with Formation of Ring Carbon-Heteroatom (P, S) Bonds, Leading to Organic Functional Materials Materials sulfur phosphorus sulfoxide <i>thia</i>-Friedel-Crafts-Bradsher <i>phospha</i>-Friedel-Crafts-Bradsher cyclization |
| title | The <i>hetero</i>-Friedel-Crafts-Bradsher Cyclizations with Formation of Ring Carbon-Heteroatom (P, S) Bonds, Leading to Organic Functional Materials |
| title_full | The <i>hetero</i>-Friedel-Crafts-Bradsher Cyclizations with Formation of Ring Carbon-Heteroatom (P, S) Bonds, Leading to Organic Functional Materials |
| title_fullStr | The <i>hetero</i>-Friedel-Crafts-Bradsher Cyclizations with Formation of Ring Carbon-Heteroatom (P, S) Bonds, Leading to Organic Functional Materials |
| title_full_unstemmed | The <i>hetero</i>-Friedel-Crafts-Bradsher Cyclizations with Formation of Ring Carbon-Heteroatom (P, S) Bonds, Leading to Organic Functional Materials |
| title_short | The <i>hetero</i>-Friedel-Crafts-Bradsher Cyclizations with Formation of Ring Carbon-Heteroatom (P, S) Bonds, Leading to Organic Functional Materials |
| title_sort | i hetero i friedel crafts bradsher cyclizations with formation of ring carbon heteroatom p s bonds leading to organic functional materials |
| topic | sulfur phosphorus sulfoxide <i>thia</i>-Friedel-Crafts-Bradsher <i>phospha</i>-Friedel-Crafts-Bradsher cyclization |
| url | https://www.mdpi.com/1996-1944/13/21/4751 |
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