Nature Communications

Table 1 Optimization of reaction conditions

From: Metal-free para-selective C-H amination and azidation of N-arylhydroxylamines

Entry^[a]	conditions					Yield (%)^[b]
Entry^[a]	Solvent	Base	T (^oC)		3	1a′	1a′′
1	MeCN	Et₃N	0		21	18	<5
2	MeCN	DBU	0		9	18	<5
3	MeCN	DMAP	0		24	15	<5
4	MeCN	K₂CO₃	0		29	23	<5
5	MeCN	NaHCO₃	0		17	5	<5
6	MeCN	Na₂CO₃	0		33	18	<5
7	DCM	Na₂CO₃	0		17	13	<5
8	THF	Na₂CO₃	0		23	23	<5
9	MeCN/THF(1/1)	Na₂CO₃	0		36	18	<5
10	MeCN/1,4-Dioxane (1/1)	Na₂CO₃	0		45	13	0
11	MeCN/1,4-Dioxane (3/1)	Na₂CO₃	0		49	18	0
12	MeCN/1,4-Dioxane (3/1)	Na₂CO₃	−20		66	13	0
13	MeCN/1,4-Dioxane (3/1)	Na₂CO₃	-40		55	13	0
14^[c]	MeCN/1,4-Dioxane (3/1)	Na₂CO₃	−20		66	18	0
15^[d]	MeCN/1,4-Dioxane (3/1)	Na₂CO₃	-20		54	15	0

^aReaction conditions: 1a (0.2 mmol, 1.0 equiv.), 2a (0.4 mmol, 2.0 equiv.), FSIT (0.3 mmol, 1.5 equiv.), base (0.4 mmol, 2.0 equiv.) in solvent at a specific temperature for 3 h. ^bIsolated yield. ^cAtmosphere of N₂ was used. ^d1.2 equivalents of FSIT were used. FSIT fluorosulfuryl imidazolium triflate, DBU 1,8-Diazabicyclo[5.4.0]undec-7-ene, DMAP 4-Dimethylaminopyridine.

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