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Please login to access the full content or check if you have access via18.15.1.2.3 Method 3: Trifluoromethylation of Arenes and Hetarenes
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Il'chenko, A. Y., Science of Synthesis, (2005) 18, 1142.
Tetrahalomethanes are widely used in the syntheses of trifluoromethylated arenes and hetarenes.[62–65] The iodo groups of iodoarenes are substituted upon interaction with trifluoroiodomethane (9) and copper in a polar aprotic solvent, giving (trifluoromethyl)arenes in good yields (Scheme 13).[49,66] Thus, (trifluoromethyl)benzene (22) is obtained in 74% yield when iodobenzene, trifluoroiodomethane (9), and copper in dimethylformamide are heated in a stainless-steel tube (Scheme 13).[66,67] Reaction of 1-iodo-2,3,5,6-tetramethylbenzene with trifluoroiodomethane (9) and copper in dimethylformamide at 150°C gives 2,3,5,6-tetramethyl-1-(trifluoromethyl)benzene in 65% yield.[68] 1-(Trifluoromethyl)naphthalene and 2-(trifluoromethyl)quinoline are also obtained in good yields by this method.[43,69]
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(Meeeeeeeeeeeeee)eeeeee(M) eee ee eeeeeeee eeee eeeeee(M) eeeee, eeee ee eeeeee(M) eeeeeeee, eeeeeee, ee eeeeee, eee eee(eeeeeeeeeeeeeee)eeeeeee(MM), eeeeeeee eeee eeeeeeeeeeeeeeeeeeeeee 88 (MM8M8, M = Me, Me) eee eeeeeee.[88] (Meeeeeeeeeeeeee)eeeeee(M) eeeeeeee ee eeee eeeeee eeeeee eeee eeeeeeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeee ee eeee eee eeeeeeeeeeeee (eeeeeeeeeeeeeee)eeeeee 88 ee eeee eeeeee (Meeeee 88).[88]
Mee eeeeeeeeeeeeeeeeeeee ee eeeeeee ee eeeeeeeeeeeeeeeeeeee (8) eee eeeeeee eeeee eeeeeeeeeee eeeee (eeeeeeeeeeeeeee)eeeeeee (88) ee 88% eeeee (Meeeee 88).[88] Meeeeee ee eeeeeeeeeeeeeeeeeeee (8) eeee eeeeeeeeeeeee[88], eeeeeeeeeeee[88], ee eeeeeeeeeee[88] ee e eeeeee eeee ee 888–888°M eeeeeeee eeeeeeee ee eee eeeeeeeeeeeee 8-, 8-, eee 8-eeee(eeeeeeeeeeeeeee)eeeeeeee. Meeeeeeeeeeee eeeeeeeeeeeeeeeeeeee ee eeeeeeee ee eeeeeeeeeeeeeeeeeeee (8) eeeee e eeeeeee ee 8-, 8-, eee 8-(eeeeeeeeeeeeeee)eeeeeeeee (88) (Meeeee 88).[88]
Meeeee 88 Meeeeeeeeeeee eee Meeeeee Meeeeeeeeeeeeeeeeeee ee Meeeeee eee Meeeeeee ee Meeeeeeeeeeeeeeeeeee[88,88]
Meeeee eeeeeeeeeeeee eeeeee eeee eeeeee ee eee eeeeeeee ee e eeeeeeee ee eeeee eeeeeeeeeeeeeeeeeee eeeeeeeee. Mee eeeeeee, eeeeeeee ee eeeeee eeeeeeeeeeeee eee eeeeeeee eeeeeeeeeee eeee 8,8,8-eeeeeeeeeeeeeeee eeeee 8-(eeeeeeeeeeeeeee)-8,8,8-eeeeeeeeeeeeeeee,[88] eeeee eeeeeeee eeeee eee eeeeeeee ee eeeeeeee eeeee ee eeeeeeee eeee eeeeeeee(MMM) eeeeeeee, ee eeee 8-(eeeeeeeeeeeeeee)-8,8,8-eeeeeeeeeeeeeeee ee 88% eeeee.[88] Mee eeeeeeeeeeee ee e eeeeeeeeeeeeeee eeeee eeee eeeeee, e eeeeee-eeee eeeeee eeeee ee eee eeeeee ee eeeeee eeeeeeeeeeeee eee eeeeeeee eeeeeeee eee ee eeee (Meeeee 88).[88] Meee eeeeeeee ee eeeeeee ee ee ee e Meeeeee–Meeeee eeee eee ee eeeeeee ee eeeeee eee eeeeeeeeeee ee eeeeeeee-eeeeeeeeeee eeeeee. (Meeeeeeeeeeeeee)eeeeeee (88) ee eeeeeeee ee eeee eeeeee ee 88% eeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeeeeeeeeeeeeee ee Meeeeee ee Meeeee Meeeeeeeeeeee eee Meeeeeee Meeeeeee[88]
References
| [43] | Meeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [49] | MeMeeeeeee, M. M. M.; Meeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [62] | Meeeeeeeeee, M. M.; Me'eeeeee, M. M., Me Meeeee Meeeeeeeee Meeeeee, Meeeeee M: Meeeeeeee Meeeeee, Mee'eee, M. M., Me.; MMM: Meeeeeeee, (8888); Mee. 8, e 888. |
| [63] | Meeeeeeeeee, M. M., Meeeeeee eee Meeeeeeeeeee Meeeeeeee eeee Meeeeeee-Meeeeeeeee Meeeeeeeeeee, Meeeeee Meeee: Meee, (8888). |
| [64] | MeMeeeeee, M. M.; MeMeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [65] | Meeeeeee, M. M.; Meeeeeeeee, M., Mee. Meee. Meeeee. Mee., (8888) 88, 888. |
| [66] | Meeeeeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
| [67] | Meeeeeeee, M.; Meeeeeee, M.; Meee, M.; Meee, M.; Meeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
| [68] | Meeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeeeee, M. M., Me. Mee. Meee., (8888) 88, 8888; Meee. Meeee., (8888) 88, 888888. |
| [69] | Meeee, M.; Meeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 88. |
| [70] | Meeeeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 888. |
| [71] | Meeeeeee, M. M.; Meeee, M. M.; Meeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [72] | Meeeee, M. M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [73] | Meeeee, M. M.; Meeeeeeee, M., M. Meeeeeee Meee., (8888) 88, 888. |
| [74] | Meeeeeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeeeeee, M.-M.; Meeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
| [75] | Meee, M.; Meee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [76] | Meeeeeeeeee, M. M.; Meeeeeeeeeeee, M. M., Me. Meeeee. Meee., (8888) 88, 8888; Meee. Meeee., (8888) 88, 88888. |
| [77] | Meeeeee, M.; Meeeee, M., M. Meeeeeee Meee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e8, 888.
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