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Practical Solvent‐Free Ruthenium Trichloride‐Mediated Benzannulation Approach to Fused Functionalized Arenes
Author(s) -
Jacquet Jeremy,
Auvinet AnneLaure,
Mandadapu Anil Kumar,
Haddad Mansour,
RatovelomananaVidal Virginie,
Michelet Véronique
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500186
Subject(s) - ruthenium , chemistry , catalysis , combinatorial chemistry , benzene , cycloaddition , atom economy , ligand (biochemistry) , benzene derivatives , solvent , organic chemistry , chemical synthesis , biochemistry , receptor , in vitro
The solvent‐ and ligand‐free [2+2+2] ruthenium‐promoted cycloaddition of α,ω‐diynes and alkynes provides a facile and efficient strategy for the synthesis of substituted benzene‐derived systems. The search for the optimal reaction conditions revealed the unprecedented catalytic activity of ruthenium trichloride for benzannulation reactions and this atom‐economical process allowed the synthesis of fused arenes including dihydrobenzofurans, isoindolines, indanes in good to high yields. This practical protocol also gave rise to the preparation of pentasubstituted aromatic derivatives and was applied to the one‐gram scale synthesis of a functionalized heterocycle.