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Selective Radical Amination of Aldehydic C(sp2)-H Bonds with Fluoroaryl Azides via Co(II)-Based Metalloradical Catalysis: Synthesis of N-Fluoroaryl Amides from Aldehydes under Neutral and Nonoxidative Conditions.

ABSTRACT: The Co(II) complex of the D2h-symmetric amidoporphyrin 3,5-Di t Bu-IbuPhyrin, [Co(P1)], has proven to be an effective metalloradical catalyst for intermolecular amination of C(sp2)-H bonds of aldehydes with fluoroaryl azides. The [Co(P1)]-catalyzed process can employ aldehydes as the limiting reagents and operate under neutral and non-oxidative conditions, generating nitrogen gas as the only byproduct. The metalloradical aldehydic C-H amination is suitable for different combinations of aldehydes and fluoroaryl azides, producing the corresponding N-fluoroaryl amides in good to excellent yields. A series of mechanistic studies support a stepwise radical mechanism for the Co(II)-catalyzed intermolecular C-H amination.

SUBMITTER: Jin LM 

PROVIDER: S-EPMC4111259 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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Selective Radical Amination of Aldehydic C(sp<sup>2</sup>)-H Bonds with Fluoroaryl Azides via Co(II)-Based Metalloradical Catalysis: Synthesis of <i>N</i>-Fluoroaryl Amides from Aldehydes under Neutral and Nonoxidative Conditions.

Jin Li-Mei LM   Lu Hongjian H   Cui Yuan Y   Lizardi Christopher L CL   Arzua Thiago N TN   Wojtas Lukasz L   Cui Xin X   Zhang X Peter XP  

Chemical science 20140601 6

The Co(II) complex of the <i>D</i><sub>2h</sub>-symmetric amidoporphyrin 3,5-Di <i><sup>t</sup></i> Bu-IbuPhyrin, [Co(<b>P1</b>)], has proven to be an effective metalloradical catalyst for intermolecular amination of C(sp<sup>2</sup>)-H bonds of aldehydes with fluoroaryl azides. The [Co(<b>P1</b>)]-catalyzed process can employ aldehydes as the limiting reagents and operate under neutral and non-oxidative conditions, generating nitrogen gas as the only byproduct. The metalloradical aldehydic C-H  ...[more]

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