Chemoselective Amination of Propargylic C(sp3)H Bonds by Cobalt(II)-Based Metalloradical Catalysis

Highly chemoselective intramolecular amination of propargylic C(sp3)H bonds has been demonstrated for N‐bishomopropargylic sulfamoyl azides through cobalt(II)‐based metalloradical catalysis. Supported by D2h‐symmetric amidoporphyrin ligand 3,5‐DitBu‐IbuPhyrin, the cobalt(II)‐catalyzed CH amination...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-07, Vol.53 (27), p.7028-7032
Main Authors: Lu, Hongjian, Li, Chaoqun, Jiang, Huiling, Lizardi, Christopher L., Zhang, X. Peter
Format: Article
Language:English
Subjects:
Additives
alkynes
Alkynes - chemistry
Amination
Byproducts
Carbon - chemistry
Catalysis
chemoselectivity
cobalt
Cobalt - chemistry
Coordination Complexes - chemistry
Derivatives
heterocycles
homogeneous catalysis
Hydrogen - chemistry
Ligands
Pargyline - analogs & derivatives
Pargyline - chemistry
Propylamines - chemistry
Synthesis
Tolerances
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Summary:Highly chemoselective intramolecular amination of propargylic C(sp3)H bonds has been demonstrated for N‐bishomopropargylic sulfamoyl azides through cobalt(II)‐based metalloradical catalysis. Supported by D2h‐symmetric amidoporphyrin ligand 3,5‐DitBu‐IbuPhyrin, the cobalt(II)‐catalyzed CH amination proceeds effectively under neutral and nonoxidative conditions without the need of any additives, and generates N2 as the only byproduct. The metalloradical amination is suitable for both secondary and tertiary propargylic CH substrates with an unusually high degree of functional‐group tolerance, thus providing a direct method for high‐yielding synthesis of functionalized propargylamine derivatives. Make a ring of it: Highly chemoselective intramolecular amination of propargylic C(sp3)H bonds has been achieved with a high degree of functional‐group tolerance through the title reaction. The [Co(P1)]‐catalyzed CH amination proceeds under neutral and nonoxidative conditions without the need of any additives, thus providing a direct method for efficient synthesis of functionalized propargylamine derivatives with N2 as the only by‐product.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201400557