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Ni‐Catalyzed Cyclization of Enynes and Alkynylboronates: Atom‐Economical Synthesis of Boryl‐1,4‐dienes
Author(s) -
CabreraLobera Natalia,
Quirós M. Teresa,
Buñuel Elena,
Cárdenas Diego J.
Publication year - 2019
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.201903405
Subject(s) - catalysis , phosphine , chemistry , salt (chemistry) , ligand (biochemistry) , combinatorial chemistry , carbon atom , atom (system on chip) , bicyclic molecule , reaction conditions , boron , reaction mechanism , atom economy , medicinal chemistry , carbon fibers , organic chemistry , ring (chemistry) , materials science , computer science , parallel computing , biochemistry , receptor , composite number , composite material
We report a novel atom‐economical Ni‐catalyzed cyclization reaction of enynes with alkynylboronates. The reaction employs a non‐expensive Ni salt, a phosphine‐based ligand and easy‐handling alkynylboronates as boron–carbon source. The reaction provides complex fused‐bicyclic compounds containing borylated 1,4‐cyclohexadienes in high yields in short reaction times, involving the formation of two C−C bonds in one step. A reasonable reaction mechanism is proposed based on mechanistic experimental results.