Tandem Blaise/Palladium-Catalyzed Ullmann Coupling for the One-Pot Synthesis of Enamino Ester-Functionalized Biaryls from Nitriles

Zi Xuan, Ju Hyun Kim, Sang Gi Lee

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10 Scopus citations

Abstract

A novel Pd-catalyzed Ullmann-type homocoupling reaction of the Blaise reaction intermediate generated by the reaction of 2-bromo arylnitriles and a Reformatsky reagent has been developed for one-pot synthesis of enamino ester-functionalized biaryls 2 in good yields. The 2,2′-substituted enamine moieties of the coupling products could be cyclized under acidic conditions through the conjugate addition/deamination cascade to afford the seven-membered N-heterocyclics 3 with biaryl backbone in excellent yields.

Original languageEnglish
Pages (from-to)7824-7829
Number of pages6
JournalJournal of Organic Chemistry
Volume80
Issue number15
DOIs
StatePublished - 7 Aug 2015

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

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