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

Table 3

Synthesis of N,N-diallylanilines from various anilines and allyl bromide^a.

Entry	R of Anilines		Time (h)	Yield (%)^b
1	1a	H	2	2a [22], 86	Trace
2	1b	2-CH3	4	2b [23], 68	Trace
3	1c	3-CH3	1	2c [24], 96	—^c
4	1d	4-CH3	1.5	2d [23], 98	—^c
5	1e	2,4-(CH3)2	2	2e [23], 92	Trace
6	1f	2-CH3O	1.5	2f [23], 91	—^c
7	1g	4-CH3O	1	2g [23], 99	—^c
8	1h	2,5-(CH3O)2	2	2h [25], 93	Trace
9	1i	3-Cl	3.5	2i [25], 76	3i [25], 23
10	1j	4-Cl	3.5	2j [22], 77	3j [22], 10
11	1k	4-Br	3.5	2k [20], 78	3k [20], 20
12	1l	2,5-Cl2	6	Trace	3l [26], 74
13	1m	3-NO2	5	2m [26], 80	3m [27], 15
14	1n	4-NO2	6	Trace	3n [22], 42
15	1o	2-NO2	6	Trace	3o [28], 38
16	1p	4-Cl-2-NO2	24	Trace	3p, 37
17	1q	2,4-Cl2-6-NO2	24	NR

^aReaction conditions: anilines (0.5 mmol), allyl bromide (1.5 mmol), K₂CO₃ (2 mmol), C₂H₅OH (2 mL), H₂O (1 mL), 70°C, TLC detection.
^bIsolated yield; all known products are characterised thoroughly by NMR, IR, MS, and elemental analysis, which were consistent with literature data.
^cNot observed.