Abstract
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 ZnCl2 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.
Original language | English |
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Pages (from-to) | 772-776 |
Number of pages | 5 |
Journal | Bulletin of the Korean Chemical Society |
Volume | 44 |
Issue number | 9 |
DOIs | |
State | Published - Sep 2023 |
Bibliographical note
Publisher Copyright:© 2023 Korean Chemical Society, Seoul & Wiley-VCH GmbH.
Keywords
- Negishi coupling
- alkynylation
- flow chemistry
- regioselectivity
- zincation