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. Author manuscript; available in PMC: 2022 Sep 1.
Published in final edited form as: J Am Chem Soc. 2021 Aug 16;143(34):13759–13768. doi: 10.1021/jacs.1c05769

Table 2.

Reaction Optimizationa

graphic file with name nihms-1801038-t0009.jpg
entry Cu base (mol %) solvent yield (SM %)b ee (%)c
1 Cu(MeCN)4BF4 A (20) PhMe 50% (49) 90
2 “ A (20), CsF (100) “ 83% (13) 90
3 “ CsF (150) “ 75% (11) 91
4 Cu(MeCN)4BF4 “ THF 39% (48) 74
5 “ “ dioxane 65% (20) 91
6 “ “ cyclohexane 50% (31) 87
7 “ “ MTBE 75% (10) 92
8 “d “ “ 74% (<1) 91
9 Cu(MeCN)4OTfd “ “ 82% (4) 90
10 CuOTf·1/2C6H6 CsF (160) 98% (–) 90
a

Standard conditions: 1a (0.10 mmol, 1.0 equiv), 2 (0.135 mmol, 1.35 equiv), [Cu] (5 mol %), L (6 mol %), solvent (1.5 mL), 32 °C, 24 h. A = NaO(2-OMeC6H4).

b

Yield was determined by 19F NMR of crude reaction, using PhF as an internal standard.

c

Determined by HPLC with a chiral stationary phase.

d

MeCN removed before reaction.