Transition-Metal-Free Fluoroarylation of Diazoacetamides: A Complementary Approach to 3-Fluorooxindoles

Abstract

An efficient transition-metal-free fluoroarylation reaction of N-aryl diazoacetamides with NFSI (N-fluorobenzenesulfonimide) is described. This reaction directly provides 3-fluorooxindole derivatives in yields of 67-93% with high selectivity via a carbene-free process under mild reaction conditions.

Organocatalytic Asymmetric Mannich Addition of 3-Fluorooxindoles to Dibenzo[b,f][1,4]oxazepines: Highly Enantioselective Construction of Tetrasubstituted C–F Stereocenters

“…The 3-fluorooxindoles 1 were obtained as method A described in the literature . The identity of known compounds 1 were confirmed by comparison with the characterization data of the literatures . Dibenzo­[ b , f ]­[1,4]­oxazepines 2a–2i were prepared as those oxazepines substituted in positions 7 and 8 and 2j–2l were prepared as those substituted in positions 1–4 described in the literature, comparing with the characterization data of the literatures to identify the known compounds 2 (except 2j and 2l ). ,, Chiral squaramide catalysts C1–C10 were prepared according to the reported procedures .…”

Designs and Strategies for the Halo‐Functionalization of Diazo Compounds

“…Qiu and Xu et al. reported the first transition metal‐free fluoroarylation of diazoacetamides 42 using NFSI ( 55 ) for the synthesis of 3‐fluorooxindole derivatives 70 (Scheme ) . This protocol provided a direct access to 3‐fluorooxindole derivatives 70 via 42’ in good yields and with high selectivity.…”

Selectfluor and Its Analogs Electrophilic Fluorination for Preparing Alkyl Fluorides

“…The transition-metal-free fluoroarylation of a-diazoacetamides was also described; the choice of the solvent and the base appeared crucial to reach reasonable yields of products (Eq. 49) [93,94]. Interestingly, the tandem cyclization fluorination is very fast in acetonitrile at 0 C with potassium carbonate as base (Eq.…”