Sulfenylation of alcohols with sulfinic acids^a.

Entry	1	2	Product 3		Yieldb (%)
1	1a	2a		3aa, Ar = Ph	90
2	1b	2a		3ba, Ar = PMP	83
3	1c	2a		3ca, Ar = 4-ClC6H4	89
4	1d	2a		3da, X = (CH2)2	91
5	1e	2a		3ea, X = O	81
6	1f	2a		3fa, X = S	77
7	1g	2a		3ga, R = Ph	65
8	1h	2a		3ha, R = 4-MeC6H4	69
9	1i	2a		3ia, R = Bn	0
10	1j	2a	RCH = CHSPh	3ja, R = Ph	43
11	1k	2a		3ka, R = 2-naphthyl	56
12	1a	2b		3ab, R = 4-MeC6H4	91
13	1a	2c		3ac, R = 4-tBuC6H4	88
14	1a	2d		3ad, R = 4-MeOC6H4	85
15	1a	2e		3ae, R = 4-FC6H4	93
16	1a	2f		3af, R = 4-ClC6H4	89
17	1a	2g		3ag, R = 4-BrC6H4	86
18	1a	2h		3ah, R = 4-IC6H4	81
19	1a	2i		3ai, R = 3-O2NC6H4	90
20	1a	2j		3aj, R = 2,4-Cl2C6H4	83
21	1a	2k		3ak, 1-naphthyl	98
22	1a	2l		3al, 2-naphthyl	99
23	1a	2m		3am, Me(CH2)7	72
24	1a	2n		3an, Bn	76
25	1a	2o		3ao, CH3	67

^aReaction conditions: alcohol 1 (0.20 mmol), sulfinic acid 2 (0.30 mmol), NaI (0.30 mmol), TsOH·H₂O (0.040 mmol), DCE (1.0 mL), 80 °C, 24 h.

^bIsolated yield.