Integrated continuous‐flow/batch protocol for ortho ‐selective alkynylation of (hetero)aryl tosylates

The ortho ‐selective alkynylation of polyhalo‐substituted (hetero)aryl tosylates was investigated using an integrated continuous‐flow/batch protocol. Without the elimination of the tosyloxy group, the regioselective ortho ‐metalation of the (hetero)aryl tosylates employing n ‐BuLi and ZnCl 2 was suc...

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Bibliographic Details
Published in:Bulletin of the Korean Chemical Society 2023, 44(9), , pp.772-776
Main Authors: Ju, Eun‐Hae, Lee, Min‐Jung, Song, Jiwoo, Kwon, Yong‐Ju, Kim, Won‐Suk
Format: Article
Language:English
Subjects:
화학
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Summary:The ortho ‐selective alkynylation of polyhalo‐substituted (hetero)aryl tosylates was investigated using an integrated continuous‐flow/batch protocol. Without the elimination of the tosyloxy group, the regioselective ortho ‐metalation of the (hetero)aryl tosylates employing n ‐BuLi and ZnCl 2 was successfully achieved in continuous‐flow chemistry within 10.92 s (residence time). The Pd‐catalyzed Negishi alkynylations of various iodoethynyl (hetero)arenes and the resulting arylzinc species proceeded at room temperature in yields ranging from 51% to 95%. Finally, the synthetic utility of this strategy was validated by the synthesis of benzofuran and pyridofuran derivatives.
ISSN:1229-5949
0253-2964
1229-5949
DOI:10.1002/bkcs.12717