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A Simple Route to New Phenanthro‐ and Phenanthroid‐Fused Thiazoles by a PIFA‐Mediated (Hetero)biaryl Coupling Reaction
Author(s) -
Moreno Isabel,
Tellitu Imanol,
Domínguez Esther,
SanMartín Raúl
Publication year - 2002
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 - 10.1002/1099-0690(200207)2002:13<2126::aid-ejoc2126>3.0.co;2-a
Subject(s) - chemistry , regioselectivity , aryl , combinatorial chemistry , ring (chemistry) , coupling (piping) , coupling reaction , reaction conditions , series (stratigraphy) , stereochemistry , computational chemistry , organic chemistry , catalysis , paleontology , biology , mechanical engineering , alkyl , engineering
An application of the PIFA‐mediated [PIFA: phenyliodine(III) bis(trifluoroacetate)] biaryl coupling reaction is presented and extended to the formation of heterobiaryl connections. A preliminary study of the scope and limitations of this procedure was carried out in the synthesis of phenanthroids 11 from a series of phenethyl‐substituted heterocycles 10 . It was observed that in some cases a competitive dimerization process took place. It was also found that the coupling step could be efficiently extended to a larger number of examples if an aromatic ring were situated fused to the 1,2‐diarylethane skeleton, as in 23 and 30 . The synthesis of a series of 4,5‐diarylthiazoles 23a − g was therefore carried out to explore the electronic requirements and the regioselectivity of the PIFA‐mediated non‐phenolic coupling reaction. When the same procedure was applied to aryl‐heteroarylthiazoles 30 , a series of phenanthroid‐fused thiazoles 31 was obtained in good overall yields. To the best of our knowledge, no oxidative aryl‐heteroaryl coupling reaction of this type had previously been reported. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)