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. 2019 Apr 25;9(6):5268–5278. doi: 10.1021/acscatal.9b00918

Table 1. Optimization of the Asymmetric C–H Arylation of Complex 1a with 2a.

2.1.

Entry Conditions Yield 3aa (%)a er3aab Yield 4aa (%)a
1c Pd(PPh3)4, 1-AdCO2H 41 – 31
2 Pd(dba)2, 1-AdCO2H 0 – 0
3 Pd(dba)2, 1-AdCO2H, 2 equiv TMP 28 38:62 9
4 Pd(CH3CN)4(BF4)2, 1-AdCO2H, 2 equiv TMP 28 36:64 7
5 Pd(CH3CN)4(BF4)2, Cy2CHCO2H, 2 equiv TMP 39 18:82 33
6d Pd(CH3CN)4(BF4)2, Cy2CHCO2H, 2 equiv TMP 43 16:84 39
7d Pd(CH3CN)4(BF4)2, 2 equiv TMP 24 55:45 2
8d,e Pd(CH3CN)4(BF4)2, Cy2CHCO2H, 2 equiv TMP 0 – 0
9d,f Pd(CH3CN)4(BF4)2, Cy2CHCO2H, 2 equiv TMP 40 19:81 27
a

Determined by 1H NMR spectroscopy using 1,3,5-trimethoxybenzene as internal standard.

b

Determined by HPLC (Chiralpak IB hexane/isopropyl alcohol).

c

Reaction carried out without L1.

d

Reactions carried out with 2 equiv of ArI.

e

Reaction carried out without Ag2CO3.

f

Reaction carried out without K2CO3.