Table 1. Chiral ligand- vs. chiral base-catalyzed asymmetric C(sp3)–H arylation a .
| ||||
Entry | L | Brønsted acid RYO2H | e.r. (yield) | ref. |
1 | Chiral NHC or phosphine | Achiral RCO2H | Up to 99 : 1 | Kündig5 |
Up to 97 : 3 | Kagan6 | |||
Up to 98 : 2 | Cramer7a | |||
2 | None | 65 : 35 (Traces) | Kagan6 | |
3 | IPr | 71 : 29 (20%) | Cramer7a | |
4 | PCy3 | 3,3′-CF3Ph-BPA | Up to 98 : 2 | This work |
aIPr = 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene; BPA = binol-derived phosphoric acid.