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

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

SN - 1523-7060

VL - 3

SP - 1435

EP - 1437

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -