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A ZnI2-catalyzed regioselective cascade 1,4-conjugate addition/5-exo-dig annulation pathway for one-pot access to heterobiaryl frameworks

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Abstract

Facile access to π-extended heterobiaryl compounds via a non-cross-coupling strategy has been achieved. In the presence of an inexpensive ZnI2 catalyst and versatile propargylamine and β-naphthol (or β-naphthylamine and β-naphthyl mercaptan) starting materials, a variety of sterically hindered heterobiaryl frameworks can be easily obtained. The present catalytic system offers excellent selectivity, good-to-excellent product yields, and good functional group tolerance including, for instance, –CN, –COOH, –C(O)R, –Br and –Cl groups. This cyclization process is proposed to proceed via in situ generated alkynyl O-quinone methides (O-AQMs), following a cascade intermolecular 1,4-conjugate addition/5-exo-dig annulation/1,3-H shift pathway.

Graphical abstract: A ZnI2-catalyzed regioselective cascade 1,4-conjugate addition/5-exo-dig annulation pathway for one-pot access to heterobiaryl frameworks

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Publication details

The article was received on 12 Sep 2019, accepted on 18 Nov 2019 and first published on 21 Nov 2019


Article type: Communication
DOI: 10.1039/C9CC07054K
Chem. Commun., 2019, Advance Article

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    A ZnI2-catalyzed regioselective cascade 1,4-conjugate addition/5-exo-dig annulation pathway for one-pot access to heterobiaryl frameworks

    X. He, P. Y. Choy, M. P. Leung, O. Y. Yuen, T. Liu, Y. Shang and F. Y. Kwong, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC07054K

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