Table 1.

Methylation of Model System^a

entry	R =	kMe	khyd	kMe/kMeH
1a	H	4.6 ± 0.1 × 10−5	2.8 ± 0.2 × 10−6	1
1b	3-F	3.1 ± 0.1 × 10−2	1.1 ± 0.1 × 10−3	670
1c	5-F	1.6 ± 0.2 × 10−4	NDb	3.5
1d	5-CF3	2.83 ± 0.03 × 10−3	6.0 ± 0.1 × 10−4	60
1e	6-CF3	4.63 ± 0.08 × 10−3	8.7 ± 0.2 × 10−4	100
1f	5-NO2	5.6 ± 0.1 × 10−3	2.2 ± 0.1 × 10−2	120
1g	4-CN	2.47 ± 0.06 × 10−3	3.3 ± 0.2 × 10−4	50
1h	5-CN	5.13 ± 0.07 × 10−3	3.9 ± 0.1 × 10−3	110
1i	6-CN	5.8 ± 0.2 × 10−3	2.1 ± 0.1 × 10−3	125

^aReactions were conducted in d₆-DMSO at 25.0 ± 0.5 °C and were monitored by ¹H NMR spectroscopy at 500 MHz.

^bND = not determined.