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Transition‐Metal‐Free Direct Synthesis of Tetra‐ and Pentacyclic Azaheteroarenes via [3+3] Annulation of Nitroarenes and Benzyl‐Type Carbanions Mediated by Silylating Agents.
Author(s) -
Nowacki Michał,
Wojciechowski Krzysztof
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601128
Subject(s) - carbanion , annulation , reagent , chemistry , tetra , adduct , transition metal , combinatorial chemistry , polymer chemistry , organic chemistry , medicinal chemistry , catalysis
Benzylic‐type carbanions react with nitroarenes under mild conditions in the presence of DBU and trialkylchlorosilanes to form tetra‐and pentacyclic azaarenes. The reaction proceed via transformation of the σ H ‐adduct formed from carbanion and nitroarene. Reaction proceed under mild conditions at room temperature and does not require transition‐metal reagents at any stage of the process.