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. Author manuscript; available in PMC: 2020 Nov 10.
Published in final edited form as: Org Lett. 2020 Jul 10;22(15):5822–5827. doi: 10.1021/acs.orglett.0c01895

Scheme 3. (A) Reaction Profile Monitored by 19F NMRa and (B) Mechanistic Information from Control Experimentsb.

Scheme 3.

aCrude reactions analyzed by 1H and 19F NMR with C6F6 as the internal chemical shift reference set at −161.64 ppm in CDCl3. bReagents and conditions for imine 3 (1.0 equiv) with arenes 5b, 5d, 5h, and 5i (2.0 equiv) at rt: (a) AgOTf or Ag2CO3 (Ag+, 1.5 equiv) in CDCl3, no reaction observed; (b) TfOH (30 mol %) in CDCl3; (c) 4 Å molecular sieves (50 wt %) in CDCl3; (d) 4 Å molecular sieves (50 wt %) with (R)-TRIP (10 mol %) in CDCl3 for 24 h, C3/C2 rr of 86:14, (+)-4d er determined by chiral NP-HPLC analysis.