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2-, 3-, and 4-(Trifluoromethoxy)phenyllithiums: Versatile Intermediates Offering Access to a Variety of New Organofluorine Compounds

✍ Scribed by Eva Castagnetti; Manfred Schlosser

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 257 KB
Volume: 2001
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200102)2001:4<691::aid-ejoc691>3.0.co;2-a

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✦ Synopsis

Consecutive treatment of (trifluoromethoxy)benzene with sec-butyllithium and electrophilic reagents affords previously inaccessible ortho-substituted derivatives in generally excellent yields. 2-(Trifluoromethoxy)phenyllithium acts as the key intermediate. The 3-and 4-isomers can readily be generated from the corresponding 3-and 4-bromo precursors by halogen-metal interconversion with butyllithium or tertbutyllithium. Upon trapping of the 2-, 3-and 4-(trifluoromethoxy)phenyllithiums with 11 different electrophiles the

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