Table 1.

Optimization of reaction conditions for the atroposelective hydroarylation of 1-alkynylindole 1a

Entry	L	Reaction conditions	Yield (%)a	ee (%)b
1	L1	DCE, 40 °C, 5 min	96	8
2	L2	DCE, 40 °C, 5 min	97	12
3	L3	DCE, 40 °C, 35 min	97	43
4	L4	DCE, 40 °C, 5 min	98	42
5	L5	DCE, 40 °C, 5 min	97	44
6	L6	DCE, 40 °C, 20 min	95	43
7	L7	DCE, 40 °C, 5 min	96	5
8	L8	DCE, 40 °C, 15 min	97	26
9	L9	DCE, 40 °C, 10 min	98	30
10	L10	DCE, 40 °C, 5 min	97	35
11	L11	DCE, 40 °C, 5 min	97	19
12	L12	DCE, 40 °C, 5 min	96	23
13	L13	DCE, 40 °C, 5 min	97	60
14	L14	DCE, 40 °C, 5 min	98	90
15	L14	CH2Cl2, 40 °C, 5 min	97	66
16	L14	toluene, 40 °C, 5 min	98	79
17	L14	THF, 40 °C, 5 min	98	84
18	L14	DCE, 10 °C, 2 h	99	93
19	L14	DCE, −10 °C, 21 h	98	96
20c	L14	DCE, −10 °C, 22 h	98	94

Reaction conditions: 1a (0.05 mmol), Cu(CH₃CN)₄PF₆ (0.005 mmol), L (0.006 mmol), solvent (2 mL), −10–40 °C, 5 min–21 h, in vials; ^aMeasured by ¹H NMR using 1,3,5-trimethoxybenzene as the internal standard; ^bDetermined by HPLC analysis; ^cWith Cu(CH₃CN)₄PF₆ (0.0025 mmol) and L14 (0.003 mmol).