AI Article Synopsis
- A new mild base, TMPZnCl.LiCl, enables the efficient preparation of various aryl and heteroaryl zinc reagents in THF through direct zincation.
- This process allows for the metalation of activated arenes and heteroarenes at room temperature.
- Importantly, the method can tolerate sensitive functional groups like aldehydes and nitro groups, broadening the possibilities for directed metalations.
Article Abstract
A wide range of polyfunctional aryl and heteroaryl zinc reagents were efficiently prepared in THF via direct zincation using TMPZnCl.LiCl, a new exceptionally mild and efficient base. Activated arenes and heteroarenes are metalated at room temperature. Remarkably, sensitive functions such as an aldehyde as well as a nitro group are tolerated, expanding significantly the scope of directed metalations.
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| http://dx.doi.org/10.1021/ol900342a | DOI Listing |
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Palladium-Catalyzed Zinc-Amide-Mediated C-H Arylation of Fluoroarenes and Heteroarenes with Aryl Sulfides.
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Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan).
C-H arylation of polyfluoroarenes and heteroarenes with aryl sulfides proceeds smoothly with the aid of a palladium-N-heterocyclic carbene catalyst. A bulky zinc amide, TMPZnCl⋅LiCl, plays a key role as an effective base to generate the corresponding arylzinc species in situ. This arylation protocol is practically much easier to perform than our previous method, which necessitates preparation of the arylzinc reagents in advance from the corresponding aryl halides.
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