Iron(II) Phthalocyanine-Catalyzed Homodimerization and Tandem Diamination of Diazo Compounds with Primary Amines: Access to Construct Substituted 2,3-Diaminosuccinonitriles in One-Pot

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7718 - 7726

Опубликована: Май 24, 2024

We herein first report the homodimerization and tandem diamination of diazo compounds with primary amines catalyzed by iron(II) phthalocyanine (PcFe(II)), which can construct one C-C bond two C-N bonds within 20 min in one-pot. Compared to traditional metal-catalyzed N-H insertion reaction between reagents, developed almost does not generate product, but homodimerization/tandem product. The proposed mechanism studies indicate that play a crucial role homocoupling via dimerization iron(III)-acetonitrile radical generated from diazoacetonitrile PcFe(II) coordinated bis(amines); β-hydride elimination is involved, then, attack toward carbon atoms on formed followed. Moreover, this novel be used effectively prepare substituted 2,3-diaminosuccinonitriles high yields even up >99:1 d.r., encouragingly these products contain both 1,2-diamines succinonitrile motifs, are classes important organic significant applications many yields. This also suitable for gram-scale preparation 2,3-bis(phenylamino)succinonitrile (

Язык: Английский

Three-component modular synthesis of chiral 1,3-dioxoles via Rh-catalyzed carbenic olefination cascade

Chemical Science, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Chiral 1,3-dioxoles are efficiently assembled from readily available I III /P V hybrid ylides reagents, aldehydes and carboxylic acids via Rh-catalyzed carbenic olefination cascade.

Язык: Английский