Synthesis of Ortho Substituted Arylboronic Esters by in Situ Trapping of Unstable Lithio Intermediates
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Synthesis of Ortho Substituted Arylboronic Esters by in Situ Trapping of Unstable Lithio Intermediates. / Kristensen, Jesper Langgaard; Lysén, M.; Vedsø, Per; Begtrup, M.
In: Organic Letters, Vol. 3, No. 10, 17.05.2001, p. 1435-1437.Research output: Contribution to journal › Letter › Research › peer-review
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TY - JOUR
T1 - Synthesis of Ortho Substituted Arylboronic Esters by in Situ Trapping of Unstable Lithio Intermediates
AU - Kristensen, Jesper Langgaard
AU - Lysén, M.
AU - Vedsø, Per
AU - Begtrup, M.
PY - 2001/5/17
Y1 - 2001/5/17
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0000984083&partnerID=8YFLogxK
U2 - 10.1021/ol015598+
DO - 10.1021/ol015598+
M3 - Letter
AN - SCOPUS:0000984083
VL - 3
SP - 1435
EP - 1437
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 10
ER -
ID: 45438179