Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes
The construction of carbon–carbon bonds by direct involvement of two unactivated carbon–hydrogen bonds, without any directing group, ensures a high atom economy of the entire process. Here, we describe a simple protocol for the Pd(II)/Cu(II)-promoted intermolecular cross-dehydrogenative coupling (CD...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-06-01
|
| Series: | Catalysts |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4344/11/7/762 |
| _version_ | 1797528985307971584 |
|---|---|
| author | Marco Lessi Attilio Nania Melania Pittari Laura Lodone Angela Cuzzola Fabio Bellina |
| author_facet | Marco Lessi Attilio Nania Melania Pittari Laura Lodone Angela Cuzzola Fabio Bellina |
| author_sort | Marco Lessi |
| collection | DOAJ |
| description | The construction of carbon–carbon bonds by direct involvement of two unactivated carbon–hydrogen bonds, without any directing group, ensures a high atom economy of the entire process. Here, we describe a simple protocol for the Pd(II)/Cu(II)-promoted intermolecular cross-dehydrogenative coupling (CDC) of 5-arylimidazoles, benzimidazoles, benzoxazole and 4,5-diphenylimidazole at their C-2 position with functionalized styrenes. This specific CDC, known as the Fujiwara–Moritani reaction or oxidative Heck coupling, also allowed the C-4 alkenylation of the imidazole nucleus when both 2 and 5 positions were occupied. |
| first_indexed | 2024-03-10T10:07:00Z |
| format | Article |
| id | doaj.art-e570a50101ae42a0a50538893b8f8192 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T10:07:00Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-e570a50101ae42a0a50538893b8f81922023-11-22T01:28:30ZengMDPI AGCatalysts2073-43442021-06-0111776210.3390/catal11070762Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with StyrenesMarco Lessi0Attilio Nania1Melania Pittari2Laura Lodone3Angela Cuzzola4Fabio Bellina5Dipartimento di Chimica e Chimica Industriale, Via Moruzzi 13, 56124 Pisa, ItalyDipartimento di Chimica e Chimica Industriale, Via Moruzzi 13, 56124 Pisa, ItalyDipartimento di Chimica e Chimica Industriale, Via Moruzzi 13, 56124 Pisa, ItalyDipartimento di Chimica e Chimica Industriale, Via Moruzzi 13, 56124 Pisa, ItalyDipartimento di Chimica e Chimica Industriale, Via Moruzzi 13, 56124 Pisa, ItalyDipartimento di Chimica e Chimica Industriale, Via Moruzzi 13, 56124 Pisa, ItalyThe construction of carbon–carbon bonds by direct involvement of two unactivated carbon–hydrogen bonds, without any directing group, ensures a high atom economy of the entire process. Here, we describe a simple protocol for the Pd(II)/Cu(II)-promoted intermolecular cross-dehydrogenative coupling (CDC) of 5-arylimidazoles, benzimidazoles, benzoxazole and 4,5-diphenylimidazole at their C-2 position with functionalized styrenes. This specific CDC, known as the Fujiwara–Moritani reaction or oxidative Heck coupling, also allowed the C-4 alkenylation of the imidazole nucleus when both 2 and 5 positions were occupied.https://www.mdpi.com/2073-4344/11/7/762C-H activationimidazolesFujiwara–Moritani reactiondehydrogenative couplingoxidative Heck couplingstyrenes |
| spellingShingle | Marco Lessi Attilio Nania Melania Pittari Laura Lodone Angela Cuzzola Fabio Bellina Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes Catalysts C-H activation imidazoles Fujiwara–Moritani reaction dehydrogenative coupling oxidative Heck coupling styrenes |
| title | Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes |
| title_full | Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes |
| title_fullStr | Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes |
| title_full_unstemmed | Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes |
| title_short | Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes |
| title_sort | palladium catalyzed dehydrogenative c 2 alkenylation of 5 arylimidazoles and related azoles with styrenes |
| topic | C-H activation imidazoles Fujiwara–Moritani reaction dehydrogenative coupling oxidative Heck coupling styrenes |
| url | https://www.mdpi.com/2073-4344/11/7/762 |
| work_keys_str_mv | AT marcolessi palladiumcatalyzeddehydrogenativec2alkenylationof5arylimidazolesandrelatedazoleswithstyrenes AT attilionania palladiumcatalyzeddehydrogenativec2alkenylationof5arylimidazolesandrelatedazoleswithstyrenes AT melaniapittari palladiumcatalyzeddehydrogenativec2alkenylationof5arylimidazolesandrelatedazoleswithstyrenes AT lauralodone palladiumcatalyzeddehydrogenativec2alkenylationof5arylimidazolesandrelatedazoleswithstyrenes AT angelacuzzola palladiumcatalyzeddehydrogenativec2alkenylationof5arylimidazolesandrelatedazoleswithstyrenes AT fabiobellina palladiumcatalyzeddehydrogenativec2alkenylationof5arylimidazolesandrelatedazoleswithstyrenes |