Palladium-Catalyzed Aminomethylamination and Aromatization of Aminoalkenes with Aminals via C-N Bond Activation
Thanks to the facile imine-enamine tautomerization, the β,γ-unsaturated hydrazones have been successfully utilized as surrogates of aminodienes for realizing the Pd-catalyzed tandem aminomethylamination/aromatization reaction with aminals via C-N bond activation. This direct and operationally simple protocol provides a fundamentally novel strategy to synthesize aromatic heterocycles from alkenes in the absence of external oxidant and base. Mechanistic studies suggested that aminal not only functioned as an aminomethyl source but also acted as formal oxidant and inner base to promote the aromatization.
Stereoselective synthesis of cis- or trans-3,5-disubstituted pyrazolidines via pd-catalyzed carboamination reactions: Use of allylic strain to control product stereochemistry through N-substituent manipulation
The stereoselective synthesis of either trans- or cis-3,5-disubstituted pyrazolidines is accomplished via Pd-catalyzed carboamination reactions of unsaturated hydrazine derivatives. The products are obtained in good yield with up to >20:1 diastereoselectivity. Stereocontrol is achieved by modulating the degree of allylic strain in the transition state for syn-aminopalladation through a simple modification of the substrate N2-substituent. The pyrazolidine products can be further transformed to 3,5-disubstituted pyrazolines via deprotection/oxidation, or to substituted 1,3-diamines via N-N bond cleavage.
Giampietro, Natalie C.,Wolfe, John P.
supporting information; experimental part
p. 12907 - 12911
(2009/03/12)
RCM-mediated synthesis of fluorinated cyclic hydrazines
A series of fluorinated cyclic hydrazine derivatives has been prepared in a straightforward manner using ring-closing metathesis (RCM) of fluorinated- and trifluoromethylated olefins as the key step. Georg Thieme Verlag Stuttgart.
De Matteis, Valeria,Van Delft, Floris L.,Tiebes, J?rg,Rutjes, Floris P. J. T.
p. 351 - 354
(2008/09/16)
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