Synthesis of Ortho Substituted Arylboronic Esters by in Situ Trapping of Unstable Lithio Intermediates

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Jesper Langgaard Kristensen, M. Lysén, Per Vedsø, M. Begtrup

matrix presented Ortho lithiation-in situ boration using lithium 2,2,6,6-tetramethylpiperidide (LTMP) in combination with triisopropylborate (B(OiPr) ) 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.
Original languageEnglish
JournalOrganic Letters
Volume3
Issue number10
Pages (from-to)1435-1437
Number of pages3
ISSN1523-7060
DOIs
Publication statusPublished - 17 May 2001

ID: 45438179