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

Eun Hae Ju, Min Jung Lee, Jiwoo Song, Yong Ju Kwon, Won Suk Kim

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

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 languageEnglish
Pages (from-to)772-776
Number of pages5
JournalBulletin of the Korean Chemical Society
Volume44
Issue number9
DOIs
StatePublished - Sep 2023

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) (NRF‐2022R1F1A1074510, NRF‐2022R1I1A1A01071676, NRF‐2021R1A6A1A10039823, NRF‐2019M1A2A2072417) and the Ministry of Oceans and Fisheries, Korea (20200610, KOPRI Grant PM22030).

Publisher Copyright:
© 2023 Korean Chemical Society, Seoul & Wiley-VCH GmbH.

Keywords

  • Negishi coupling
  • alkynylation
  • flow chemistry
  • regioselectivity
  • zincation

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