Integrated continuous-flow/batch protocol for ortho-selective alkynylation of (hetero)aryl tosylates
- 주제(키워드) alkynylation , flow chemistry , Negishi coupling , regioselectivity , zincation
- 등재 SCOPUS
- 발행기관 John Wiley and Sons Inc
- 발행년도 2023
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000211686
- 본문언어 영어
- Published As https://doi.org/10.1002/bkcs.12717
초록/요약
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. © 2023 Korean Chemical Society, Seoul & Wiley-VCH GmbH.
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