Compound 5m

(R)-N-(4-bromophenyl)-3-chloro-2-fluoro-6-(1-fluoroethyl) benzamide

From: Controlling Pd(iv) reductive elimination pathways enables Pd(ii)-catalysed enantioselective C(sp3)−H fluorination

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Compound data: HPLC

Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

5m was prepared from 3m following general procedure C described for compound 5a (91% ee). The ee value was determined by HPLC analysis on a Chiralcel AS-H column (10% isopropanol in hexanes, 0.5 mL/min) with retention time of 15.5 min (minor) and 17.4 min (major). Absolute stereochemistry was assigned based on the X-ray crystallographic data of compound 5a. 1H NMR (600 MHz, CDCl3): δ 7.58 (s, 1H), 7.55 (t, 1H), 7.51 (br s, 4H), 7.37 (d, J = 8.4 Hz, 1H), 5.90 (dq, J = 47.1, 6.4 Hz, 1H), 1.69 (dd, J = 24.1, 6.4 Hz, 3H). 13C NMR (150 MHz, CDCl3): δ 160.97, 154.30 (d, J = 249.4 Hz), 141.26 (dd, J = 20.4, 1.6 Hz), 136.06, 132.43, 132.23, 123.52 (dd, J = 17.7, 5.1 Hz), 122.43 (dd, J = 9.3, 4.1 Hz), 121.82, 121.47 (dd, J = 18.8, 2.1 Hz), 118.10, 87.95 (dd, J = 168.5, 2.2 Hz), 23.04 (d, J = 24.9 Hz). 19F NMR (376 MHz, CDCl3): δ –116.90, –167.43. HRMS (ESI-TOF): m/z calculated for C15H12BrClF2NO+ [M+H]+ 373.9753, found 373.9751.

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