Sulfonylation of alcohols with sulfinic acids^b.

Entry	1	2	Product		Yieldb (%)
1	1a	2a		4aa, Ar = Ph	86
2	1b	2a		4ba, Ar = PMP	93
3	1c	2a		4ca, Ar = 4-ClC6H4	88
4	1d	2a		4da, X = (CH2)2	90
5	1f	2a		4fa, X = S	81
6	1g	2a		4ga	75
7	1j	2a		4ja	67
8	1a	2b		4ab, R = 4-MeC6H4	91
9	1a	2c		4ac, R = 4-tBuC6H4	85
10	1a	2d		4ad, R = 4-MeOC6H4	82
11	1a	2e		4ae, R = 4-FC6H4	73
12	1a	2f		4af, R = 4-ClC6H4	87
13	1a	2k		4ak, 1-naphthyl	90
14	1a	2l		4al, 2-naphthyl	95
15	1a	2m		4am, Me(CH2)7	63

^aReaction conditions: alcohol 1 (0.20 mmol), sulfinic acid 2 (0.30 mmol), NaI (0.30 mmol), TsOH·H₂O (0.040 mmol), MeNO₂ (1.0 mL), 80 °C, 24 h.

^bIsolated yield.