Preparation of Polyfunctional Arylzinc Organometallics in Toluene by Halogen/Zinc Exchange Reactions |
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Authors: | Moritz Balkenhohl Dorothe S Ziegler Alexandre Desaintjean Leonie J Bole Alan R Kennedy Eva Hevia Paul Knochel |
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Institution: | Moritz Balkenhohl,Dorothée S. Ziegler,Alexandre Desaintjean,Leonie J. Bole,Alan R. Kennedy,Eva Hevia,Paul Knochel |
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Abstract: | A wide range of polyfunctional diaryl‐ and diheteroarylzinc species were prepared in toluene within 10 min to 5 h through an I/Zn or Br/Zn exchange reaction using bimetallic reagents of the general formula R′2Zn?2 LiOR (R′=sBu, tBu, pTol). Highly sensitive functional groups, such as a triazine, a ketone, an aldehyde, or a nitro group, were tolerated in these exchange reactions, enabling the synthesis of a plethora of functionalized (hetero)arenes after quenching with various electrophiles. Insight into the constitution and reactivity of these bimetallic mixtures revealed the formation of highly active lithium diorganodialkoxyzincates of type R′2Zn(OR)2Li2]. |
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Keywords: | alkoxides lithium metal/halogen exchange organozinc reagents toluene |
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