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Synthetic Applications of the Nickel‐Catalyzed Cyclization of Alkynes Combined with Addition Reactions in a Domino Process
Author(s) -
Durandetti Muriel,
Hardou Lucie,
Lhermet Rudy,
Rouen Mathieu,
Maddaluno Jacques
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100967
Subject(s) - synthon , domino , chemistry , stereoselectivity , catalysis , reagent , moiety , nickel , combinatorial chemistry , cascade reaction , organic chemistry
Carbonickelations of alkynes and functionalization of the resulting vinylnickel moiety have been performed efficiently in a nickel‐catalyzed domino cyclization–condensation process. This reaction, which does not require the preparation of any other organometallic reagent, proceeds only by exo ‐dig cyclization. This convenient and mild method constitutes a one‐pot synthesis of substituted dihydrobenzofurans, chromans, isochromans, indoles, or indanes. Theses valuable products are generally obtained in good yields and high stereoselectivity. They are shown to be useful synthons for rapid access to functionalized polycyclic skeletons.