Integrated continuous-flow/batch protocol for ortho-selective alkynylation of (hetero)aryl tosylates
2023
Ju, E.H. | Lee, M.J. | Song, J.W. | Kwon, Y.J. | Kim, W.S.
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.
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