期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 9, 期 14, 页码 3209-3215出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200204373
关键词
aromatic substitution; arynes; biaryls; metalation; nucleophilic substitution
Noncatalyzed coupling reactions of aryllithiums and haloarenes proceed not only through the well-known aryne route but also, in some cases, through a novel addition-elimination pathway. Indeed, ortho-chloro- and ortho-bromomethoxyarenes lead selectively to the corresponding ortho-biaryls through a chelation-driven aromatic nucleophilic substitution pathway. Contrary to common belief, such noncatalyzed coupling reactions often proceed with high regioselectivity and high yield. These results underline the potency of such simple reactions and open up a straightforward access to a wide range of biaryl structures; this also appears particularly useful for large-scale and biaryl building-block syntheses, as only cheap and readily available substrates are involved.
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