Synthesis of ortho substituted arylboronic esters by in situ trapping of unstable lithio intermediates.
Identifieur interne : 000203 ( PubMed/Checkpoint ); précédent : 000202; suivant : 000204Synthesis of ortho substituted arylboronic esters by in situ trapping of unstable lithio intermediates.
Auteurs : J. Kristensen [Danemark] ; M. Lysén ; P. Veds ; M. BegtrupSource :
- Organic letters [ 1523-7060 ] ; 2001.
Abstract
[reaction: see text] Ortho lithiation-in situ boration using lithium 2,2,6,6-tetramethylpiperidide (LTMP) in combination with triisopropylborate (B(OiPr)(3)) is a highly efficient and experimentally straightforward process for the preparation of ortho substituted arylboronic esters. The mild reaction conditions allow the presence of functionalities such as ester or cyano groups or halogen substituents that are usually not compatible with the conditions used in directed ortho metalation of arenes. The arylboronic esters underwent Suzuki-type cross-coupling with a range of aryl halides, furnishing biaryls in 53-94% yield.
PubMed: 11388835
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<front><div type="abstract" xml:lang="en">[reaction: see text] Ortho lithiation-in situ boration using lithium 2,2,6,6-tetramethylpiperidide (LTMP) in combination with triisopropylborate (B(OiPr)(3)) is a highly efficient and experimentally straightforward process for the preparation of ortho substituted arylboronic esters. The mild reaction conditions allow the presence of functionalities such as ester or cyano groups or halogen substituents that are usually not compatible with the conditions used in directed ortho metalation of arenes. The arylboronic esters underwent Suzuki-type cross-coupling with a range of aryl halides, furnishing biaryls in 53-94% yield.</div>
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<ArticleTitle>Synthesis of ortho substituted arylboronic esters by in situ trapping of unstable lithio intermediates.</ArticleTitle>
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<Abstract><AbstractText>[reaction: see text] Ortho lithiation-in situ boration using lithium 2,2,6,6-tetramethylpiperidide (LTMP) in combination with triisopropylborate (B(OiPr)(3)) is a highly efficient and experimentally straightforward process for the preparation of ortho substituted arylboronic esters. The mild reaction conditions allow the presence of functionalities such as ester or cyano groups or halogen substituents that are usually not compatible with the conditions used in directed ortho metalation of arenes. The arylboronic esters underwent Suzuki-type cross-coupling with a range of aryl halides, furnishing biaryls in 53-94% yield.</AbstractText>
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