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Zirconium‐Mediated Intramolecular Coupling of Terminal Alkynes and Their Subsequent Carbonylation: Novel Synthesis of Seven‐ and Eight‐Membered Heterocycles
Author(s) -
Barluenga José,
Sanz Roberto,
Fañanás Francisco J.
Publication year - 1997
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.19970030820
Subject(s) - intramolecular force , alkyne , carbonylation , zirconium , chemistry , coupling (piping) , molecule , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , materials science , carbon monoxide , metallurgy
The development of a new method for the intramolecular coupling of terminal alkynes and for the synthesis of seven‐ and eight‐membered benzoheterocycles is reported. The key steps involve the generation of zirconocene‐alkyne complexes from 2‐bromoalkenes and the subsequent intramolecular carbometalation of olefins or acetylides. The 8‐unsubstituted zirconabicyclopentenes were carbonylated to afford unexpected products and allow access to polyfunctionalized molecules from simple starting materials.