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Ortho metalation directed by α-amino alkoxides. An improved synthesis of ortho-substituted aryl ketones

✍ Scribed by Daniel L. Comins; Jack D. Brown

Book ID
104226288
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
215 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

Ortho-substituted aryl ketones are prepared from N-[2-(dimethylamino)ethy]-Nmethylbenzamides via ortho lithiation of intermediate a-amino alkoxides, formed in situ by addition of RLi. also described. An ortho lithiation of N-[2-(dimethylamino)ethyl]-N-methylbenzamide is Tertiary a-amino alkoxides, formed in situ by the addition of an organolithium reagent to a tertiary arylcarboxamide, can be ortho-lithiated and alkylated to provide orthosubsituted aryl ketones.lm3 This method works well for the directed a-metalation of thiophenesl and furans2 due to their ease of deprotonation. Gschwend and co-workers3 have , * --s_s 14. C. R. Noller and R. Adams, J. Am. Chem. Sot., _, 46 1889 (1924). 15. The amino amide was added to set-BuLi/TMEDA in THF at -78°C. -

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The reaction of ct,13-unsaturated ketones 1 with an excess of lithium powder, a catalytic amount of naphthalene (4 %) and different carbonyl compounds in the presence of boron trifluoride in THF at -78 -0°C yields, after treatament with silyl nucleophile and final hydrolysis, the expected substitute