Substrate-controlled product divergence in the reaction of α-fluoro-β-ketoamides with arynes

Abstract

An interesting substrate-controlled reactivity switch has been observed in the reaction of α-fluoro-β-ketoamides with arynes. The reaction of secondary α-fluoro-β-ketoamides with aryne provided access to α-aryl-α-fluoroacetamides through an arylation/deacylation sequence....

Chemodivergence in Fluorine Source-Controlled Cascade Reaction of Aryne Precursors to Synthesize Pyrrolo[3,4-b]indoles and 3-Arylated Maleimides

“…Reaction strategies allowing chemodivergence represent one of the most cutting-edge developments in synthetic organic chemistry and pharmaceutical chemistry . A huge number of organic molecules with novel architectures were obtained from the same reactants by adjusting the reaction parameters . The development of this strategy will significantly expand the molecular diversity yet remains a formidable challenge.…”

Chemoselective α-Trifluoroacetylation of Amides Using Highly Electrophilic Trifluoroacetic Anhydrides and 2,4,6-Collidine

“…Tsuji–Trost reaction of 3aa proceeded smoothly under mild conditions to give α,α-disubstituted β-ketoamide 9 in 89% yield. The interaction of 3aa with benzyne, which was generated in situ from 2-(trimethylsilyl)­phenyl triflate, gave tetrasubstituted ( E )-alkene 10 in 63% yield. The configuration was determined by X-ray structural analysis (CCDC 2272276).…”