Catalyst-Free and Highly Selective N,N-Diallylation of Anilines in Aqueous Phase

Table 1

Optimization of the reaction conditions of aniline with allyl bromide^a.

Entry	Base (mmol)	Temp (°C)	Solvent (mL)	Time (h)	Yield (%)^b
					2a [22]	3a [22]
1	None	70	C2H5OH (3)	5.5	14	32
2	Na2CO3 (2)	70	C2H5OH (3)	5.5	54	16
3	NaHCO3 (2)	70	C2H5OH (3)	5.5	59	Trace
4	K2CO3 (2)	70	C2H5OH (3)	5.5	86	Trace
5	K2CO3 (1.5)	70	C2H5OH (3)	5.5	65	8
6	K2CO3 (2.5)	70	C2H5OH (3)	5.5	74	Trace
7	K2CO3 (2)	RT	C2H5OH (3)	7	35	35
8	K2CO3 (2)	40	C2H5OH (3)	6.5	68	31
9	K2CO3 (2)	70	C2H5OH/H2O (2/1)	2	86	Trace
10	K2CO3 (2)	70	C2H5OH/H2O (1/1)	2	49	19
11	K2CO3 (2)	70	C2H5OH/H2O (1/2)	2	57	4
12	K2CO3 (2)	70	H2O (3)	2	30	23

^aReaction conditions: aniline (0.5 mmol), allyl bromide (1.5 mmol), and TLC detection.
^bIsolated yield by column chromatography. The products are known and characterised thoroughly by NMR, IR, MS, and elemental analysis, which were consistent with literature data.