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Accessing Heteroannular Benzoxazole and Benzimidazole Scaffolds via Carbodiimides Using Azide–Isocyanide Cross-Coupling as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived from a Phenothiazine Moiety
[Image: see text] The coupling of aryl and aliphatic azides with isocyanides yielding carbodiimides (8–17) were efficiently catalyzed by well-defined structurally characterized trans-(MIC)PdI(2)(L) [MIC = 1-CH(2)Ph-3-Me-4-(CH(2)N(C(6)H(4))(2)S)-1,2,3-triazol-5-ylidene, L = NC(5)H(5) (4), MesNC (5)],...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10061513/ https://www.ncbi.nlm.nih.gov/pubmed/37008148 http://dx.doi.org/10.1021/acsomega.2c07875 |
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author | Dey, Shreyata Ghosh, Prasenjit |
author_facet | Dey, Shreyata Ghosh, Prasenjit |
author_sort | Dey, Shreyata |
collection | PubMed |
description | [Image: see text] The coupling of aryl and aliphatic azides with isocyanides yielding carbodiimides (8–17) were efficiently catalyzed by well-defined structurally characterized trans-(MIC)PdI(2)(L) [MIC = 1-CH(2)Ph-3-Me-4-(CH(2)N(C(6)H(4))(2)S)-1,2,3-triazol-5-ylidene, L = NC(5)H(5) (4), MesNC (5)], trans-(MIC)(2)PdI(2) (6), and cis-(MIC)Pd(PPh(3))I(2) (7) type palladium complexes, which incidentally mark the first instances of the use of mesoionic singlet palladium carbene complexes for the said application. As observed from the product yields, the catalytic activity varied in the order 4 > 5 ∼ 6 > 7 for these complexes. A detailed mechanistic studies indicated that the catalysis proceeded via a palladium(0) (4a–7a) species. Using a representative palladium precatalyst (4), the azide–isocyanide coupling was successfully extended to synthesizing two different bioactive heteroannular benzoxazole (18–22) and benzimidazole (23–27) derivatives, thereby broadening the scope of the catalytic application. |
format | Online Article Text |
id | pubmed-10061513 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-100615132023-03-31 Accessing Heteroannular Benzoxazole and Benzimidazole Scaffolds via Carbodiimides Using Azide–Isocyanide Cross-Coupling as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived from a Phenothiazine Moiety Dey, Shreyata Ghosh, Prasenjit ACS Omega [Image: see text] The coupling of aryl and aliphatic azides with isocyanides yielding carbodiimides (8–17) were efficiently catalyzed by well-defined structurally characterized trans-(MIC)PdI(2)(L) [MIC = 1-CH(2)Ph-3-Me-4-(CH(2)N(C(6)H(4))(2)S)-1,2,3-triazol-5-ylidene, L = NC(5)H(5) (4), MesNC (5)], trans-(MIC)(2)PdI(2) (6), and cis-(MIC)Pd(PPh(3))I(2) (7) type palladium complexes, which incidentally mark the first instances of the use of mesoionic singlet palladium carbene complexes for the said application. As observed from the product yields, the catalytic activity varied in the order 4 > 5 ∼ 6 > 7 for these complexes. A detailed mechanistic studies indicated that the catalysis proceeded via a palladium(0) (4a–7a) species. Using a representative palladium precatalyst (4), the azide–isocyanide coupling was successfully extended to synthesizing two different bioactive heteroannular benzoxazole (18–22) and benzimidazole (23–27) derivatives, thereby broadening the scope of the catalytic application. American Chemical Society 2023-03-14 /pmc/articles/PMC10061513/ /pubmed/37008148 http://dx.doi.org/10.1021/acsomega.2c07875 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Dey, Shreyata Ghosh, Prasenjit Accessing Heteroannular Benzoxazole and Benzimidazole Scaffolds via Carbodiimides Using Azide–Isocyanide Cross-Coupling as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived from a Phenothiazine Moiety |
title | Accessing Heteroannular Benzoxazole and Benzimidazole
Scaffolds via Carbodiimides Using Azide–Isocyanide Cross-Coupling
as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived
from a Phenothiazine Moiety |
title_full | Accessing Heteroannular Benzoxazole and Benzimidazole
Scaffolds via Carbodiimides Using Azide–Isocyanide Cross-Coupling
as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived
from a Phenothiazine Moiety |
title_fullStr | Accessing Heteroannular Benzoxazole and Benzimidazole
Scaffolds via Carbodiimides Using Azide–Isocyanide Cross-Coupling
as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived
from a Phenothiazine Moiety |
title_full_unstemmed | Accessing Heteroannular Benzoxazole and Benzimidazole
Scaffolds via Carbodiimides Using Azide–Isocyanide Cross-Coupling
as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived
from a Phenothiazine Moiety |
title_short | Accessing Heteroannular Benzoxazole and Benzimidazole
Scaffolds via Carbodiimides Using Azide–Isocyanide Cross-Coupling
as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived
from a Phenothiazine Moiety |
title_sort | accessing heteroannular benzoxazole and benzimidazole
scaffolds via carbodiimides using azide–isocyanide cross-coupling
as catalyzed by mesoionic singlet palladium carbene complexes derived
from a phenothiazine moiety |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10061513/ https://www.ncbi.nlm.nih.gov/pubmed/37008148 http://dx.doi.org/10.1021/acsomega.2c07875 |
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