1174638-38-0Relevant articles and documents
Keteniminium-Driven Umpolung Difunctionalization of Ynamides
Dutta, Shubham,Gandon, Vincent,Mallick, Rajendra K.,Sahoo, Akhila K.,Vanjari, Rajeshwer,Yang, Shengwen
supporting information, p. 10785 - 10790 (2020/03/13)
A three-component Pd-catalyzed coupling of ynamides, aryl diazonium salts, and aryl boronic acids for the synthesis of novel triaryl-substituted enamides is described. This transformation represents the first example of an umpolung regioselective unsymmetrical syn-1,2-diarylation/aryl-olefination of ynamides. The aryl moieties of the diazonium salt (electrophile) and boronic acid (nucleophile) are explicitly incorporated in the electrophilic α- and nucleophilic β-position, respectively, of the ynamide, resulting in a single isomer of the N-bearing tetrasubstituted olefin. The scope is broad (68 examples), showing excellent functional-group tolerance. DFT calculations substantiate the rationale of the mechanistic cycle and the regioselectivity. The chemoselectivity and synthetic potential of the enamide products were also studied.
Copper-mediated coupling of 1,1-dibromo-l-alkenes with nitrogen nucleophiles: A general method for the synthesis of ynamides
Coste, Alexis,Karthikeyan, Ganesan,Couty, Francois,Evano, Gwilherm
supporting information; experimental part, p. 4381 - 4385 (2009/10/23)
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