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. 2020 May 29;11(24):6283–6288. doi: 10.1039/d0sc01391a

Table 2. Selective optimization of the carboetherification conditions a .

Inline graphic
Entry [Pd]/L Base Solvent T (°C) Yield b , c (ee) [%]
1 Pd2(dba)3/L3 NaOtBu Toluene 80 40(87)
2 Pd2(dba)3/L3 NaOPh Toluene 80 30(38)
3 d Pd2(dba)3/L3 NaOtBu DCM 80 45(33)
4 Pd2(dba)3/L3 NaOtBu Toluene 20 55(95)
5 Pd A/L3 NaOtBu Toluene 20 51(95)
6 Pd2(dba)3/L5 NaOtBu Toluene 20 44(85)
7 Pd2(dba)3/L7 NaOtBu Toluene 20 60(96)
8 Pd2(dba)3/L8 NaOtBu Toluene 20 52(82)

aUnless otherwise specified, all reactions were carried out with 5a (0.2 mmol), 2a (1 mmol, 5 eq.), a [Pd] source (0.005 mmol, 2.5 mol%), N-Me-Xiang-Phos (0.01 mmol, 5 mol%), base (0.4 mmol, 2 eq.), and H2O (3.6 μL, 1 eq.) in a solvent (1 mL, 0.2 M).

bYield of isolated product.

cDetermined by chiral HPLC.

dPd2(dba)3 was added to 5 mol%, and L3 was added to 10 mol%.