Mechanochemical One-Pot Barbier/Simmons-Smith Reaction <i>via</i> Sequential Zinc Activation

Herein we report a mechanochemical one-pot Barbier/Simmons–Smith reaction enabled by ball-milling-mediated activation of zinc. This operationally simple method allows the <i>in situ</i> generation of organozinc intermediates and their sequential use in allylation and cyclopropanation without intermediate work-up. The protocol exhibits high chemoselectivity, broad substrate scope, and compatibility with different physical forms of zinc metal. The reaction proceeds with excellent diastereoselectivity in selected cases and was demonstrated on gram scale using standard ball milling equipment. Comparative studies highlight the advantages of this sustainable mechanochemical approach over traditional solution and neat conditions.<br>Analysis of reaction products from this methodology resulted in the following data:– ¹H, ¹⁹F and ¹³C NMR raw data files.– IR spectra– High-resolution mass spectrometry (HRMS) data