An Original L-shape, Tunable N-Heterocyclic Carbene Platform for Efficient Gold(I) Catalysis
International audience The synthesis and characterization of original NHC ligands based on an imidazo[1,5-a]pyridin-3-ylidene (IPy) scaffold functionalized with a flanking barbituric heterocycle is described as well as their use as tunable ligands for efficient gold-catalyzed C−N, C−O, and C−C bond...
Published in: | Angewandte Chemie International Edition |
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Main Authors: | , , , , , , , , |
Other Authors: | , , , , , , , , , , , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
HAL CCSD
2019
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Subjects: | |
Online Access: | https://hal.archives-ouvertes.fr/hal-02335228 https://hal.archives-ouvertes.fr/hal-02335228/document https://hal.archives-ouvertes.fr/hal-02335228/file/Angew%20Chem%20int%20Ed,%202019,%2058,%207977.pdf https://doi.org/10.1002/anie.201901090 |
Summary: | International audience The synthesis and characterization of original NHC ligands based on an imidazo[1,5-a]pyridin-3-ylidene (IPy) scaffold functionalized with a flanking barbituric heterocycle is described as well as their use as tunable ligands for efficient gold-catalyzed C−N, C−O, and C−C bond formations. High activity, regio-, chemo-, and stereoselectivities are obtained for hydroelementation and domino processes, underlining the excellent performance (TONs and TOFs) of these IPy-based ligands in gold catalysis. The gold-catalyzed domino reactions of 1,6-enynes give rise to functionalized heterocycles in excellent isolated yields under mild conditions. The efficiency of the NHC gold 5Me complex is remarkable and mostly arises from a combination of steric protection and stabilization of the cationic AuI active species by ligand 1Me. |
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