Table 1. Optimization of the Ligand Structure^a,b.

			D content (%)
entry	ligand	yield (%)	ortho	meta	para	total D content
1	L1	99	11	50	23	1.66
2	L2	95	22	73	41	2.42
3	L3	97	24.5	79	47	2.65
4	L4	98	4	46	23	1.27
5	L5	98	7	35	21	1.05
6	L6	97	5	72	46	2.08
7	L7	97	17	90	74	2.87
8c	L7	95	39	95	84	3.51
9c,d	L7	99	34	60	32	2.15
10c	no L7	98	0	0	0	0
11c,e	L7	94	62	95	95	4.05

^aReactions were performed on a 0.1 mmol scale.

^bYields and degrees of deuteration were determined by ¹H NMR spectroscopy using mesitylene as an internal standard. The total deuterium content was determined by mass spectrometry.

^cThe reaction was performed with D₂O/HFIP (7:3) as the solvent. Since D₂O is used as part of the solvent system, this corresponds to an excess of approximately 390 equiv.

^dNo 3-trifluoromethylquinoline.

^eThe reaction was performed with a reaction time of 48 h.