You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via6.1.39.5.3 Variation 3: Arylations and Alkylations of Acid Halides
Please login to access the full content or check if you have access via
Kaufmann, D. E.; Köster, M., Science of Synthesis, (2005) 6, 1225.
Ketones are available from the reaction of tetraalkyl- or trialkyl(aryl)borates with acyl halides. This reaction is very useful for obtaining ketones that are otherwise difficult to synthesize, e.g. via the Friedel–Crafts route. To suppress alkyl transfer, the use of sec-alkylboranes, such as tricyclopentylborane, is helpful. Lithium is essential as the counterion because borates, obtained from Grignard reagents and trialkylboranes, usually give O-alkylated arylketones in low yields only (Scheme 13).[17,53] Copper(I) as the counterion enhances the tendency of intermolecular transfer of organic groups.
Meeeee 88 Meeeeeeeeee ee Meeeeee eeee Meee Meeeeee eee Meeeeee Meeeeee[88,88]
Meeeeeeeeeee Meeeeeeee
Meeeee 8-Meeeeeeeeeee [88, M8 = (MM8)8MM8Me; M8 = Me]; Meeeeee Meeeeeeee:[88]
8.8 M MeMe (88.8 eM, 88 eeee) ee eeeeee eee eeeeee 8-eeeeee-8-eeeeeeeeeeee (8.88 e, 88 eeee) eeee eeeeeeeeeeee eeeee eeee 8.8 e ee 8°M ee e eeee ee eeeeeeeeeeeeeeeeeeee (88.8 e, 88 eeee) ee MMM (88 eM) eeeee M8; eee eeeeeee eee eeee eee 8 e ee 88–88°M. Meeee eeeeeeeeeee ee eee eeeeeeee, eeeeeeeeeeee eeeeeeee eeeeee 8-eeeeeeeeeeee; eeeee: 8.88 e (88%); ee 88–88°M/8.88 Meee; MM (eeee) ν̃eee: 8888, 8888, 8888 ee−8.
Mee eeeeeee eee eeeeeeeee eeee eeeeeeeee eeeee. Meeee eeeeeeeeeee ee eee eeeeeee, eeeeeeeeeee eeeeeeeeeeeeeeeeeeee (8.8 e, 88%) eee eeeeeeeee. Meeeeeeee ee eee eeeeeee eeeee eeeeeeee M8M8 ee e eeeeeeeeee eeeeeeeeeee eeeeee eee eeeeeeee eee eeeeeeeeeeeeee.
References
[17] | Meeeeee, M.; Meeeee, M.; Meeeee, M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[53] | Meeeeee, M.; Meee, M.-M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8e, 888.