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. 2017 Jul 24;13:1446–1455. doi: 10.3762/bjoc.13.142

Table 3.

Synthesis of N-(1-arylalkyl)imides 9.

graphic file with name Beilstein_J_Org_Chem-13-1446-i003.jpg
entry 1-imidoalkyltriaryl-
phosphonium salts		 ArH solvent T, °C time, h MW USa 9 yield, % o:pb
5 A R1 R
1 5b o-C6H4 Me Ph anisole – 180 2 – – 9aa+9ab 72 1.0:1.2
2 5b o-C6H4 Me Ph – 150 1 70 Wc – 66 1.0:1.1
3 5c o-C6H4 Me m-ClC6H4 – 100 3.5 – – 77 1.0:1.2
4 5c o-C6H4 Me m-ClC6H4 – 75 1 10 Wc – 78 1.0:1.1
5 5e o-C6H4 Me p-CF3C6H4 – 90 2 – – 91 1.0:1.1
6 5e o-C6H4 Me p-CF3C6H4 – 90 1 – + 78 1.0:1.1
7 5e o-C6H4 Me p-CF3C6H4 – 60 4 6 Wc – 82 1.0:1.0
8 5f o-C6H4 Ph Ph – 150 2.5 – – 9ba+9bb 58 1.0:1.6
9 5f o-C6H4 Ph Ph – 130 1 25 Wc – 60 1.0:2.8
10 5h o-C6H4 Ph p-CF3C6H4 – 90 2 – – 81 1.0:2.3
11 5h o-C6H4 Ph p-CF3C6H4 – 90 1 – + 83 1.0:1.9
12 5i o-C6H4 iBu Ph – 170 2 – – 9ca+9cb 58 1.0:3.0
13 5j o-C6H4 iBu m-ClC6H4 – 100 2 – – 88 1.0:2.1
14 5l (CH2)2 Me Ph – 195 2 – – 9da+9db 41 1.4:1.0
15 5n (CH2)2 Me p-CF3C6H4 – 140 2 – – 56 1.3:1.0
16 5b o-C6H4 Me Ph 1,3-dimethoxy-
benzene		 – 170 2.5 – – 9e 71 –
17 5c o-C6H4 Me m-ClC6H4 C6H5NO2 100 4 – – 73 –
18 5e o-C6H4 Me p-CF3C6H4 C6H5Cl 80 4 – – 76 –
19 5e o-C6H4 Me p-CF3C6H4 C6H5Cl 80 3 – + 82 –
20 5f o-C6H4 Ph Ph C6H5NO2 150 0.5 – – 9f 60 –
21 5i o-C6H4 iBu Ph – 170 2 – – 9g 76 –
22 5j o-C6H4 iBu m-ClC6H4 100 2 – – 56 –
23 5j o-C6H4 iBu m-ClC6H4 C6H5Cl 100 2 – – 63 –
24 5e o-C6H4 Me p-CF3C6H4 1,3,5-trimethoxy-
benzene		 – 110 2 – – – –d –
25 5e o-C6H4 Me p-CF3C6H4 toluene – 130 2 – – 9ha+9hb 23e 1.0:2.6
26 5e o-C6H4 Me p-CF3C6H4 – 120 0.25 – – 50f 1.0:3.4
27 5e o-C6H4 Me p-CF3C6H4 – 100 0.25 100 Wc – 46f 1.0:4.0
28 5h o-C6H4 Ph p-CF3C6H4 C6H5NO2 130 2 – – 9ia+9ib 51 1.0:2.3
29 5h o-C6H4 Ph p-CF3C6H4 C6H5NO2 120 2 140 Wc – 60 1.0:3.8

aThe exposition to ultrasound irradiation. bMolar ratio of ortho to para isomer. cThe average microwave power that provides the desired reaction temperature. d1-(2,4,6-trimethoxyphenyl)ethyltris(4-trifluoromethylphenyl)phosphonium tetrafluoroborate (10) was isolated from the reaction mixture in 73% yield as the main product. eN-Vinylphthalimide was also obtained as side product in 54% yield. fThe reaction was carried out in the presence of an equimolar amount of tetrafluoroboric acid.