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Efficient Assembly of Tetracyclic Framework of Fluorenols through Silver‐Catalyzed Tandem Reaction of Acceptor‐Enynals and Alkynes via Unfavorable 6‐ endo ‐ dig Cyclization
Author(s) -
Liang Renxiao,
Zhang Jiantao,
Chen Lianfen,
Zhu Shifa
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700613
Subject(s) - alkyne , chemistry , catalysis , friedel–crafts reaction , cycloaddition , cascade reaction , tandem , aryl , acceptor , combinatorial chemistry , organic chemistry , materials science , alkyl , physics , composite material , condensed matter physics
We present a silver‐catalyzed reaction of acceptor‐enynals with alkynes to assemble tetracyclic framework of fluorenols efficiently, in which the reaction was proposed to proceed through an unfavorable 6 ‐endo‐dig cyclization, followed by a tandem [4+2] cycloaddition/Friedel–Crafts reaction. The reaction could be conducted in one pot for diaryl alkynes substrates. For terminal aryl alkyne or arylalkyl alkyne substrates, the Friedel–Crafts reaction has to be performed in the absence of alkynes. The control reactions demonstrated that there was competition between [Ag]⋅⋅⋅alkyne and [Ag]⋅⋅⋅O=CR 2 .