An efficient method is developed for the synthesis of functionalized benzimidazoles and perimidines by the condensation of aryl diamines with β-carbonyl compounds catalyzed by ytterbium chloride. The reactions give good yields under mild conditions. A mechanism involving a lanthanide activated C-C bond cleavage is proposed.

Lanthanide-catalyzed addition of diethyl phosphite with chalcones was achieved under mild conditions. The reaction exhibited good product selectivity using different catalysts. γ -Oxophosphonates were obtained in high yields in the reactions catalyzed by Yb(OAr) 3 (THF) 2 , while those catalyzed by [(Me 3 Si) 2 N] 3 La(μ-Cl)Li(THF) 3 afforded 1,2-oxaphospholane-5-phosphonates as the main products in moderate to good yields. This methodology provides facile and practical approaches to the corresponding organophosphorus compounds with biological interest. C 2013 Wiley Periodicals, Inc. Heteroatom Chem. 24:345-354, 2013; View this article online at wileyonlinelibrary.com.

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A Facile Route to 1,5-Benzodiazepin-2-yl-phosphonates via Ytterbium ChlorideCatalyzed Three-Component Reaction. -The one-pot three-component condensation of o-diaminobenzene, diketones (II), and diethyl phosphite (III) proceeds under mild reaction conditions in the presence of a representative lanthanide catalyst to furnish the benzodiazepine-based phosphonates (IV) in moderate yields. The lower activity of aryl-substituted butane diones makes it necessary to carry out the reaction at higher temperatures to get yields comparable to those of alkyl-substituted diketones. -(JI, X.; CAI, L.; YAO, Z.; FAN*, X.; QI, S.; Heteroat. Chem. 21 (2010) 2, 89-95;

Lanthanide complexes efficiently catalyze the phospha‐Michael addition of diethyl phosphite to chalcones yielding phosphonates of type (III) or (V) depending on the ratio of the reactants.