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Synthesis and Properties of 2,3‐Dialkynyl‐1,4‐benzoquinones
Author(s) -
Hammershøj Peter,
Reenberg Theis K.,
Pittelkow Michael,
Nielsen Christian B.,
Hammerich Ole,
Christensen Jørn B.
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600081
Subject(s) - sonogashira coupling , chemistry , cyclic voltammetry , combinatorial chemistry , acceptor , electron acceptor , stereochemistry , organic chemistry , electrochemistry , palladium , catalysis , physics , electrode , condensed matter physics
Alkynyl substituents can be used to tune the acceptor properties of benzoquinones due to their slight electron‐withdrawing abilities. Applications of new acceptors rely on efficient and practical synthetic procedures. Herein we describe a general and convenient approach for the synthesis of 2,3‐dialkynyl‐1,4‐benzoquinones using a combination of regiospecific aromatic substitution, Sonogashira cross‐couplings and mild CAN oxidation chemistry. The regiochemical outcome of the synthetic protocol was verified by X‐ray crystallography of two compounds. Cyclic voltammetry, UV/Vis and DFT calculations on three derivatives show that the symmetrical dialkynyl‐substituted benzoquinones are attractive acceptors.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)