Table 1.

Optimization of Amination Conditions^a

Entry	Catalyst Loading (mol%)	Solvent	Time	Yield (%)d
1	10b	C6D6	10 min	> 99
2	5b	C6D6	20 min	> 99
3	2b	C6D6	40 min	97
4	1b	C6D6	90 min	96
5	0.1	C6D6	48 h	73
6	1b	Hexanes	90 min	95
7	1b	Et2O	90 min	96
8	1b	(d8-)Toluenee	90 min	95
9	1b	d8-THF	90 min	94
10	10	d6-DMSO	N/Ac	0
11	10	d4-Methanol	N/Ac	0
12	10	DCM	N/A	0

^aReaction were conducted on 0.2 mmol scale, see SI for details of the experiments.

^bRegeneration of 1 by ¹⁹F NMR spectroscopy.

^cCatalyst decomposition.

^dYields were determined by ¹H NMR spectroscopy using tetrakis(trimethylsilyl)silane as internal standard.

^eBoth proteo- and deutero-toluene were tested as solvent, and no difference was observed.