Skip to main content
. 2018 Jun 4;9(26):5767–5772. doi: 10.1039/c8sc02041h

Table 1. Ligand screening and reaction optimization a .

Inline graphic
Entry Ligand Solvent Base t [h] Yield b [%] er c
1 L1 DCE 48 (22) 92.5 : 7.5
2 L1 DCE Cs2CO3 48 <5 n.d.
3 L1 DCE DBU 48 <5 n.d.
4 L1 DCE i-Pr2NEt 48 72 96 : 4
5 L1 DCE Et3N 48 74 97 : 3
6 L1 DCE i-Pr2NH 48 76 97 : 3
7 L1 DCE DABCO 48 84 97.5 : 2.5
8 L2 DCE DABCO 48 <5 n.d.
9 L3 DCE DABCO 48 11 98 : 2
10 L4 DCE DABCO 48 <5 n.d.
11 L5 DCE DABCO 48 28 92 : 8
12 L1 THF DABCO 48 11 96 : 4
13 L1 CHCl3 DABCO 48 67 97 : 3
14 L1 CH2Cl2 DABCO 36 88 (86) 98 : 2

aReaction conditions: 3 mol% [Ir(COD)Cl]2, 6 mol% ligand, 0.24 mmol of 1a, 0.2 mmol of 2a and 0.2 mmol of base in 0.6 mL solvent. The catalyst was prepared via n-PrNH2 activation.

bYields were determined by 1H-NMR spectroscopy with mesitylene as the internal standard. Isolated yields are given in the parentheses.

cThe enantiomeric ratio (er) was determined by HPLC analysis on a chiral stationary phase; n.d. = not determined. DCE = 1,2-dichloroethane.