Table 2.

Substrate scope of the enantioselective C–H iodination.

A
entry	1	Ar	Alkyl	time (h)	conv.* (yield, %)†	ee (%)‡		s§
						2	3
1	1a	2-Me-Ph	Me	24	51 (48)	93	91	73.6
2	1b	2-Me-Ph	Et	24	50 (49)	91	91	67.3
3	1c	2-Me-Ph	nBu	48	47 (45)	77	87	32.9
4	1d	2-Me-Ph	iBu	48	51 (49)	83	81	25.0
5	1e	2-Me-Ph	Bn	48	47 (44)	67	75	13.8
6	1f	2-Me-Ph	cyclopropyl	24	42 (42)	70	95	83.5
7	1g	2-OMe-Ph	Me	24	49 (46)	93	97	240
8	1h	2-F-Ph	Me	24	48 (47)	89	96	148
9	1i	2-Me,4-Cl-Ph	Me	24	51 (49)	97	93	113
10	1j	3-Me-Ph	Me	24	45|| (42, mono:di=3:1)	78	92¶	99.5
11	1k	4-Me-Ph	Me	48	45 (35)	78	95	91.7
12	1l	2-naphthyl	Me	48	41 (37)	67	95	76.0
13#	1m	Ph	nBu	48	42|| (40, mono:di=1:1.4)	70	87¶ (99**)	124

B
entry	4	Ar	time (h)	conv. (yield, %)	ee (%)		s
					5	6
1	4a	Ph	48	47* (44, mono:di=2:1)	85	96‡	128
2	4b	2-Me-Ph	24	49 (49)	93	96	168
3	4c	3-Me-Ph	48	50 (44)	93	94	112
4	4d	4-OMe-Ph	48	46* (43, mono:di=3:1)	82	98‡	134
5†	4e	4-F-Ph	48	48 (41)	90	98	244
6†	4f	4-Cl-Ph	48	49 (40)	92	97	152
7†	4g	4-CF3-Ph	48	40 (38)	65	99	155

C
entry	7	Ar	time (h)	conv. (yield, %)	ee (%)		s
					8	9
1	7a	Ph	48	43* (40, mono:di=1:1)	71	87† (99‡)	88.0
2	7b	2-Me-Ph	48	50 (49)	91	92	77.2
3	7c	2-F-Ph	48	41 (41)	68	99	188
4	7d	2-naphthyl	48	43 (40)	72	96	112

^*Calculated conversion, c = ee₂/(ee₂ + ee₃).

^†Isolated yield of the iodinated product.

^‡Determined by chiral HPLC analysis.

^§Selectivity(s) = (rate of fast-reacting enantiomer)/(rate of slow-reacting enantiomer).

^||Determined by crude ¹H-NMR.

^¶ee for the mono product.

^#3 equiv. I₂ was added after 24 h.

^**ee for the di product.

^*Determined by crude ¹H-NMR.

^†3 equiv. I₂ was added after 24 h.

^‡ee for the mono product.

^*Determined by crude ¹H-NMR.

^†ee for the mono product.

^‡ee for the di product.