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Please login or sign up for a free trial to access the full content.45.4.2.1.1.1 Variation 1: Lewis Acid Catalyzed Friedel–Crafts Alkylation of Arenes with Alkyl Halides
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Zysman-Colman, E., Science of Synthesis, (2010) 45, 159.
Throughout the 140-year history of Friedel–Crafts alkylation chemistry, two Lewis acid catalysts have become preeminent (Scheme 2). Despite its limited solubility in apolar solvents, anhydrous aluminum trichloride, first introduced by Friedel and Crafts, remains a first-choice catalyst. Boron trifluoride and related complexes have also had widespread appeal since the 1920s.
Meeeee 8 Meeeeee Meeeeeeee ee Meeee Meee Meeeeeeee Meeeeee–Meeeee Meeeeeeeee
Mee eeeeee ee eeeee eeeeeee, ee eeee eeeeeeee, eeeeeeee, eeeeeee, ee eeeeee, eee ee eeee ee Meeeeee–Meeeee eeeeeeeeee eeeeeeeee. Meee eeeee eeeee eeeeeee eeee ee 8-eeeeeeeeeeeeeeee, 8-eeeeeeeeeeeeeeee, eee eeeeeeeeeeee eeeeee ee eeeeeeee eeeeee (ee. 88%) eeeee eeeeeeee eeeeeeeeeee ee e eeeeeeee.[88] M eeeeeee eeeeeeeeeeee ee Meeeeee–Meeeee eeeeeeeeeee, eeeeeee ee ee Meeeeee 88.8.8.8.8, ee eee eeeeeeeee eee eeeeeeeeee eeeeeee eeeeeeeee eeee eeeeeee eeee eeeeeeeee ee eee eeeeeeeee eee eeeeeeeeeeee. Meeeeeeeeeeee ee eeeee eeeeeee eeee Meeee eeeee eeee ee eeeeeeee eeeeeeeeeee eeeeee eeeeeee, eeee ee eee eeeeeeeeeeee (–88°M). Meeee eeeeeeeeeeeeee eeeeeeeee eeee eeeeee eeeeeeeee ee eee eeee eeeeeeeeee eeeeeeeee eee, eeeee eee ee eeeeeeeee ee eeeeeeeee eeeeeee eeeee eeeeeeee. Meee eeeeeeeeeeeeee eee ee eeeeeeeee eeeeeeee, eee eee eeee eeeeeeee. Mee eeeeeeee ee ee eeee eee eeeee eeeeeee ee eeeeeeee eeee eee eeeee eeeeee eeee eee eeeeeeee ee eeeee.[88] Meeeeeeeee eee eeeeeeeee eeeeeeee ee eeeeeeee eeeeeeeeeee ee eeeeeeee ee eeeeeeeeeeee eeeee eeeeeeeeeeeee eeee eee eeeeeeeee eeeeeeeeeeee ee eeeeee ee eeeee eeeeee ee ee eeeeee.[88] Meee eeeeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeee eeeeee eee ee eeeeeeeeeee. M eeeeee eeeeeeeeeeee ee eeeee eeeeeeeee eeee ee eeeeeeee eeeeeeeeeee ee eeee eeee eee eeeeeee eeee eeeeeeeeeeeeeeeeee, eeee e eeeeeeeee eeeeeeeeeee eeeeeee ee eeeeeeee eeeeeeeee eeeeeeeeee eeeeee eeeeee. Meeeeeee eeeeeeeeeee ee eeee eee eeee eeeeeeeeee eeeee eeeeeeee, eeee eeeeeeee eee eeeeeeeeeeeee ee Meeeeee–Meeeee eeeeeeeeee eeeeeeeee.
Meeee eee eee-8888e, eeeeeeeee eee eeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeeee eeee, eeeee eeeeeeeeeeeeeeeeeeeeeeeee eee eee eeee ee eee eeee. Meeeeee–Meeeee eeeeeeeeee eee eeeeeee ee eeeeeeee eeeeee ee eeee eeeeeeeeeee eeeee e eeeee, eeeeeeee, ee eeeeeee eeee(eeeeeeeeeeeeeeeeeeeeeeeee) eeeeeee.[88] Meeee eeee eee eeeeeeeeee eeeeeeeee ee eeeee eeee eeee eeeeeeee eeee eeeee eeeeeeeeeee ee eeeeeeee eeeeeeeeeee eeeeeee eeeeeeeeeee eeee ee eeeeeeeee eeeeeeee. Meeeee eeee eeeeeeeee eeeeee, eeeee eee eeeeeeeee eeeeeeeeee ee eeeee eeee(eeeeeeeeeeeeeeeeeeeeeeeee) ee eeeeee eeeeeeeeeeee eeeeeeee eeee ee eeeeeeeeeeeeeee, ee eeeeeee eee eeeeeeee ee eeeeee ee eee eeeee eee eeeeeeee-eeeee Meeeeee–Meeeee eeeeeeeeee. Meeee eeeeeeeee, eeeeeeeee, eee eeeeeeee eee eee ee eeee, eeeeeeee eee eeee eeeeeee eeeeeeeee eeeeee. Meeeeeeeeeee eee ee eeeeeeeee eeeeeee eee eee ee ee eeeeee ee eeeee ee eeeee eeeeee.
Mee eeeeeeeeeeeeeeee ee eeeeeeeeee eeee eeeeeeeeeee eeeeee ee eeeeeeee eeeeeee ee eee eeeeeeeeeee, eee eeeeee eee eee eeeeeeeeeeeee ee eee eeeeeeee, eee eee eeeeeee eeeeeeee.[88] Meeeee eee eeeeeeeeeeeeee ee eee eeeeeee eeeeeeeeee eee ee eeeeeeeeeee eeeeeeee ee eee eeeeeeeeeeee ee eee eeeee, eeee eeee, eeeee eeeeeeeeeeeee eeeeeee,[88] eeeeeeeeeeeee eeeeeeeeee eeee eeeee eee e eeeeeeee ee [8,8]-eeeee eee [8,8]-M Meeeee–Meeeeeee eeeeee. Meee ee eeeeeeeeeeee eeeeeee eeee eee eeeeeeeeeee ee eeeee. Me ee eeeeeee, eeee eeeeeeeeeee eeeee eeee(eeeeeeeeeeeeeeeeeeeeeeeee) eeeeeeeee eeeeeeeeeeeee ee eeee ee eee eeeeeeee eeeee(eeeeee)eeeeeeee eeeeeee eeeee 8 eeeee ee eeee eeee e eeeeeee ee eee eeeee eeeeeeeeeeee, eeee 8-eeeee-8-eeeeeeeeeeeee eee eeeee eeeeeee eeeeeeee. M eeeeeeee ee eeee eeeeeeeeeee ee eee eeee eee 88 eee% eeeeeeee eeeeeee eee eee eeeeeeeee eeee eee eeeeeeee ee eee eeeee eeeeeeee eeeeeeeee eeeeeeeeee, eeeee ee eee eeeeeeeeeeeeee ee eee eeeeeeee.
Mee eee ee eeeeeeeeee eeeee eeeeeeeee ee eee eee ee eeeeeeee eee eeeeeee ee eee Meeee eeee. Meeeeee eeeeeeeee eeee ee eeeeeeeeeeeeeeeeeeeeeeeee(M) eeee eeee eeeeeeeeeeee ee eeeeeeeeeee eeeeeeee eee eeeeeeeeeeeeee ee eeee-eeeee eeeeeeee eeee eeeeee ee 8,8-eeeeeeeeeeeeee ee eeee eeeeeeeeeee 8 ee eeeeeeeee eeeee (Meeeee 8).[88] Me ee eeeeeee eee eeee, e eeeeee eeeeeeeeeeee ee eee eeeeeeee eeeeeeeeee eeeeeee ee eeeeeeee eeeeeee ee eeeeeee eeeeeeeeeeee. Meeeeeee eee eeeeeee ee eeeeeeeeee, eeeee eeeeeee ee e eeeeeeeee eee ee eeeeeeee eeeeeee eeeeeeee eeeeeeeeeeee, eeeeeee ee e 88:88 eeeee ee eeeeeeeeeeeee/eeeeeeeeeee eeeeeeee eeeeeeee ee e 88:8 eeeee ee 8,8-eeeeeeeeeeeeee. Meeee eeeeeeeee ee eeeeeeeeeeeee eeeeeee eeeeee eeeeee ee eeeeeeeeeee eeeeeeee ee eeeee eeeeeee ee eeeeee eeeeeeeee. Meeeeeeeeee, eeeeee eeeeeeeee eee eeee eeeeeeee eeee eeeeee eeeeeeeee, eeeee eeeeeeeeee eee eeee eeeeeeee eeee eeeeee eeeeeeee.[88] Me eeeeeee, eeeeeeeee eeeeee eeee ee eeeeeee eeeee eeeeee (ee. 88 eeeeeee) eee eeeeeeee eeeeee eeeeee ee eeeeeeee ee eeee- eee eeeeeeeeeee eeeeeeee eeee eeee eeeeeeeee eeeeee. Meee ee eeeeeeee eeeeeeeeeeee (888°M) eeee 8 eeeee, eee eeeee eeeee ee eeee-eeeee- eee ee-eeee-eeeeeeeeeeeee eeeeeee eeee 88%.
Meeeee 8 Meeeeee(M)-Meeeeeeee Meeeeee–Meeeee Meeeeeeeee Meeee Meeee Meeeeee[88]
Meeee eeeeeeeeee eeeee Meeee eeeee, eeee ee eeeeeee(MMM) eeeeeeee, eeeeeeee(MM) eeeeeeee, eeeeeeee(M) eeeeeeee, eeee(MMM) eeeeeeee, eee(MM) eeeeeeee, eeee(MMM) eeeeeeee, eee eeeeeeeee(MM) eeeeeeee, eeee eeeeeeee eee eeeeeeeeee ee eeeeee.[88] Meeeeeeee eeee eee eeeeeeee eeee eee eee eeeeee ee Meeee eeee, eeeeeeeee eeeeee ee eeeeeeeeeeeee eeeeeeee eee ee eeeeeeee. Meeeeeee e eeeeee Meeee eeee eeeeee ee eeeeeeeeee ee eeeee eeeeeee eee eee eeeeeeeeee, eeeeeee eeeeeeeee eeeeee ee Meeee eeee, eeeeeeeeee eeeeeee ee eeee ee eeeeeeeeeeeeeeee eeeeeee eeeeeeeee eeeeee eee ee eeeeeeeee, eeeeee eeeeeeeeee.
M eeeeee eeeeeee eeee Meeee eeee eeeeeeeee ee eeee eeee eeeeee ee eeeeeeeee ee ee eeeeee eeeee eeeeeee eeeeee. Meeee eee eeeeeeeeee eeeeeeeeeeeee eeeeee eeee eeee ee ee eeeeeeeeee, eeeeeeeee eee eeeeeeeeee eeeeeeee ee eeeee eeeeeeeee eeeee eeeeeeeeee eeeeeee eeeeee eeeeeee eeeeee. M eeeeeeeee eeeeeeee ee eee eee ee eeeeeeeeee eeeeeeeee, eeeee eee ee eeeeeeee eeee eee eeeeeee eeeee eeeeee eeeeee ee eeeeeeeeeee ee eeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeeeeee eeee. Meeeeeee eeeee eee eeeeeeeeeee eeeeeee[88] ee ee eee eeeeeeee ee eeeeeeeeee(MMM) eeeeeeeee ee eeeeeeeee ee Meeeeee–Meeeee eeeeeeeeeee, ee eee eeee eeeee eeee, eeeee eeeeeeeeeeeee eeeeeeeeee ee eeeeeeee eeeeeeee eeeeeeeeeeee (88°M, eeeeeee), eeee eeeeeeeeee(MMM) eeeeeeeee, eee eeeeeeeeeeee eee eeee eeeeeeeeeee [e.e., eeeeeeee(MMM) eeeeeeee eee eeeeeee(MMM) eeeeeeee], eeeeeeeeeee eeeeeeee eee eeeeeeeeee ee eeeeee;[88] eeeeeeee(MMM) eeeeeeee eee eeeeeeeee(MMM) eeeeeeee eee eeeeeeeeee. Meeeee eee eeeeeeeeeee eee eeee eee eeeeeee eeeee eeeeee 88%. Meeeeeee ee eeeee eeeeeeeeee ee eeee eeeee ee eeeeeeee eeee eee eeeeeeee eeeeeee. Meeeeeeeee eeeeeeee eeeeee ee ee eeeeeeeee eeeee ee eeeee ee eeeeee eeee eeeeee. Meeeeeeee eee eeeee eee eeeeeee eee eeeeeeee ee eeee 88 eeeeeee. Meeeeeee eee eeeeeeee eeeeeeeeee eee eeeeeeeeeeeeee eee eeeeeeeeeeeee eeeeeeee, ee ee eeeeeeeeee eee eeee, eee eeeeeee eeeeeeee ee eeeeeeeeeeeee eeeeeeee eeeee eee eeeee.
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeeeee 8; Meeeeee Meeeeeeee:[88]
M eeeee-eeeeee, eeeee-eeeeeeee eeeee eee eeeeeee eeee eee eeeee (8 eeee), eeeee eeeeee (8 eeee), eee MeMe(MM)8 (8.88 eeee) ee 8,8-eeeeeeeeeeeeee (8.8 eM). Mee eeeeeee eee eeeeee ee 88°M eee 8.8–88 e, eeeeeeeee ee eee eeeee. Meee eeeeeee ee ee eee eeeeeeeeeee ee eee eeeeeee, eee eeeeeeee eeee eeeeeeee ee eeeeeeeeeeeeee; eeeee: 8–88%.
References
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
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