Nature Communications

Table 1 Optimization for transition-metal-free cross-coupling reaction between 1a and 2a^a.

From: Transition-metal-free formal cross-coupling of aryl methyl sulfoxides and alcohols via nucleophilic activation of C-S bond


Entry	Base/equiv	2a/equiv	Solvent	Assay yield^b/%
1	LiOMe/3.0	—	2-Me-THF	0
2	NaOMe/3.0	—	2-Me-THF	2
3	KOMe/3.0	—	2-Me-THF	12
4	KOMe/3.0	—	toluene	0
5	KOMe/3.0	—	DME	33
6	KOMe/3.0	—	CPME	7
7	KOMe/3.0	—	dioxane	7
8	KO^tBu/3.0	3.0	DME	67
9	K₂CO₃/3.0	3.0	DME	0
10	KOH/3.0	3.0	DME	28
11	KN(SiMe₃)₂/3.0	3.0	DME	10
12^c	KO^tBu/3.0	3.0	DME	95
13^d	KO^tBu/3.0	3.0	DME	91
14^c	KO^tBu/2.0	2.0	DME	94(90^e)
15^c	KO^tBu/2.0	1.5	DME	85
16^c	KO^tBu/1.5	2.0	DME	83
17^c,f	KO^tBu/2.0	2.0	DME	35

^aReaction conditions: 1a (0.1 mmol), 2a (0.3 mmol), base (0.3 mmol), solvent (1.0 mL) under argon atmosphere at 110 °C for 12 h.
^bAssay yield determined by ¹H NMR using 0.1 mmol (7.0 μL) CH₂Br₂ as internal standard.
^c0.5 M concentration.
^d1.0 M concentration.
^eIsolated yield.
^f80 °C.

Back to article page

Search

Advanced search

Quick links