Expedient Preparation of Aryllithium and Arylzinc Reagents from Aryl Chlorides Using Lithium 4,4′-Di-tert-Butylbiphenylide and Zinc(II) Chloride

Zhi-Liang Shen; Korbinian Sommer; Paul Knochel

doi:10.1055/s-0034-1380697

Synthesis, Table of Contents

Synthesis 2015; 47(17): 2617-2630
DOI: 10.1055/s-0034-1380697

paper

Expedient Preparation of Aryllithium and Arylzinc Reagents from Aryl Chlorides Using Lithium 4,4′-Di-tert-Butylbiphenylide and Zinc(II) Chloride

Zhi-Liang Shen

Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany Email: paul.knochel@cup.uni-muenchen.de

,

Korbinian Sommer

Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany Email: paul.knochel@cup.uni-muenchen.de

,

Paul Knochel*

Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany Email: paul.knochel@cup.uni-muenchen.de

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Abstract

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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-tert-butylbiphenylide (LiDBB) as a lithiation reagent. The resulting organometallic reagents underwent subsequent reactions with a variety of electrophiles, such as an aldehydes, DMF, PhSSO₂Ph, 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, NMe₂, 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 N,N,N′-trimethylethylenediamine (LiTMDA). The presence of a hydroxyl group was also tolerated when it was deprotonated with n-BuLi prior to the addition of LiDBB.

Key words

organolithium reagents - aryllithium - arylzinc - palladium - cross-coupling

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References

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