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- W2478267382 abstract "We report an efficient method for the preparation of aryllithium and zinc reagents from inexpensive and readily available aryl chlorides by using lithium 4,4′-di-<i>tert</i>-butylbiphenylide (LiDBB) as a lithiation reagent. The resulting organometallic reagents underwent subsequent reactions with a variety of electrophiles, such as an aldehydes, DMF, PhSSO<sub>2</sub>Ph, TsCN, an aryl halide, or an acid chloride (through Pd-catalyzed cross-coupling). Aryl chlorides bearing substituents, including methoxy, 3,4-methylenedioxy, fluoride, TMS, OTMS, NMe<sub>2</sub>, acetal, and ketal, were shown to be appropriate substrates. Interestingly, aryl chlorides containing a formyl group could also be used, provided that the formyl group was temporarily converted into an α-amino alkoxide by using the lithium amide of <i>N</i>,<i>N</i>,<i>N</i>′-trimethylethylenediamine (LiTMDA). The presence of a hydroxyl group was also tolerated when it was deprotonated with <i>n</i>-BuLi prior to the addition of LiDBB." @default.
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- W2478267382 date "2015-05-19" @default.
- W2478267382 modified "2023-10-09" @default.
- W2478267382 title "Expedient Preparation of Aryllithium and Arylzinc Reagents from Aryl Chlorides Using Lithium 4,4′-Di-tert-Butylbiphenylide and Zinc(II) Chloride" @default.
- W2478267382 doi "https://doi.org/10.1055/s-0034-1380697" @default.
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