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. 2020 May 28;5(22):12637–12648. doi: 10.1021/acsomega.9b04091

Table 2. Synthetic Methodology Comparison of Our Novel ILs vs Structurally Related, Currently Available ILs Reported in the Chemical Literature.

    intermediate IL
 IL product
  
entry class structure reaction conditions (temperature, °C; reaction time, hours, solvent and/or separation) structure reaction conditions (temperature, °C; reaction time, hours, solvent and/or separation) references
1 1. RTSi-ILs [DBU-M-TMSi] Cl 70 °C, 2 h, solvent-free [DBU-M-TMSi] NTf2 RT, 0.5 h, water this work
2   [BM-M-TMSi-im] Cl 80 °C, 12 h, NaI, CH3CN [BM-M-TMSi-im] NTf2 RT, 0.5 h, CH2Cl2, water this work
3 2. RTim-ILs [DMMB-im] Br 85 °C, 12 h, solvent-free [DMMB-im] BF4 RT, 1 h, CH2Cl2, water this work
4       [DMMB-im] NTf2 RT, 0.5 h, water this work
5 3. RTP-ILs [TBP888] Br 135 °C, 12 h, solvent-free [TBP888] NTf2 RT, 0.5 h, CH2Cl2, water this work
6 4. RTMim-ILs [ABM-im] Br 40 °C, 4 h, CH3CN [ABM-im] NTf2 RT, 0.5 h, water this work
7 5. RTim-ILs [BMO-im] Br 70 °C, 72 h, CH3CN [BMO-im] BF4 RT, 0.5 h, water this work
8       [BMO-im] PF6 RT, 0.5 h, water this work
9       [BMO-im] NTf2 RT, 0.5 h, water this work
10 DBU derivatives cf. 1. RTIL [DBU-Et] Br 60 °C, 48 h, CH3CN [DBU-Et] SCN RT, 24 h, CH2Cl2, water ref (78)
11 cf. 2. RTim-ILs [DHPA-im] Cla 130 °C, 48 h, solvent-free [DHPA-im] NTf2a RT, N/A h, ethyl acetate, CH3CN, water ref (52)
12 cf. 3. RTP-ILs [TBP] Cla 120 °C, 72 h, pet. ether, water [TBP] BF4a 60 °C, 18 h, CH2Cl2, ref (53)
13       [TBP] NTf2a 40 °C, 18 h, water; CH2Cl2 ref (53)
14   [TOP] Cla 120 °C, 72 h, pet. ether, water [TOP] NTf2a 60 °C, 18 h, ethanol/water (2:1), CH2Cl2 ref (53)
15   [P8888] Br 110 °C, 72 h, n-hexane [P8888][(EtO)HPO2] RT, 6 h, anion exchange resin (Amberlites IRN-78), water/ethanol (1:2, v/v) ref (61)
16 cf. 1. RTSi-ILs2. RTim-ILs ene-bearing ILs 110 °C, 48–72 h, toluene (or) 82 °C, 48–72 h, CH3CN ene-bearing ILs RT, 24 h, water ref (61)
17 RTILs cf. 2. RTim-ILs 4. RTMim-ILs5. RTim-ILs [OM-im] Bra 80 °C, 24 h, toluene [OM-im] F(CF2)4SO3a RT, 48 h, acetone, CH2Cl2 ref (71)
18   [TMHEDA] Br 80 °C, 12 h, toluene [TMHEDA] BF4 RT, 48 h, acetone, CH2Cl2, water ref (79)
19   [2MOPYR] Br 70 °C, N/A h, CH3CN [2MOPYR] NTf2 RT, 24 h, CH3CN, CH2Cl2, water ref (68)
20   [F(CF2)4(CH2)2mim] F(CF2)4SO3 120 °C, 0.33 h, CH2Cl2, microwave, water, 3-layer separation [F(CF2)4(CH2)2mim] F(CF2)4SO3 reflux, 4 h, dry propanol, CH2Cl2 ref (79)
21   [BCP] Bra 135 °C, 18 h, solvent-free, wash with ethyl acetate [BCP] NTf2a 70 °C, N/A h, water ref (80)
22   [iPr2N(CH2)2N112] Cl reflux, 24 h, CH3CN, Na2CO3 [iPr2N(CH2)2N112] NTf2 RT, N/A h, CH2Cl2, water ref (181)
a

Abbreviations used for IL cations retrieved from the chemical literature: [TBP]: tributyl phosphate, [TOP]: tributyl(2,3-dihydroxypropyl)phosphonium, [P8888] Br: tetraoctylphosphonium bromide, [DHPA-im]: 1-(2,3-dihydroxypropyl)-3-alkylimidazolium, [OM-im]: 1-octyl-3-methylimidazolium, [TMHEDA]: N,N,N′,N′-tetramethyl-N′-hexyl-ethylenediammonium, [2MOPYR]: 1-octyl-2-methylpyridinium, [F(CF2)4(CH2)2mim]: fluoroalkyl methylimidazolium, [iPr2N(CH2)2N112]: 1-(2-diisopropylaminoethyl)dimethylethylammonium, [BCP]: 1-butyl-4-cyanopyridinium. Other abbreviations: cf.: compare to, hr: hour/s, N/A: not available, RT: room temperature.