TY - JOUR
T1 - Suzuki aryl cross-coupling chemistry using derivatives of 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
AU - Roche, Alex J.
AU - Canturk, Belgin
N1 - Funding Information: The National Science Foundation is gratefully acknowledged for allowing the purchase of the NMR system through a Major Research Instrumentation grant (NSF CHE-0116145). Rutgers, The State University of New Jersey, Campus at Camden, is also acknowledged for generously providing startup funds. Furthermore, Shirin Modarai is thanked for her laboratory assistance.
PY - 2005/4
Y1 - 2005/4
N2 - An exploration into the scope of Suzuki aryl cross-coupling chemistry using derivatives of 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane is reported. The coupling of 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane with various aryl boronic acids and boronic acid pinacol esters was successful, with the exception of very sterically demanding systems, such as mesityl. The synthesis of the previously unreported 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophanyl-4- boronic acid is described, together with various Suzuki aryl cross-coupling reactions of this new system. Using standard Suzuki methodology, it was possible to prepare dicyclophanes bearing two octafluoro[2.2]paracyclophane units separated by both one and two benzene rings.
AB - An exploration into the scope of Suzuki aryl cross-coupling chemistry using derivatives of 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane is reported. The coupling of 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane with various aryl boronic acids and boronic acid pinacol esters was successful, with the exception of very sterically demanding systems, such as mesityl. The synthesis of the previously unreported 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophanyl-4- boronic acid is described, together with various Suzuki aryl cross-coupling reactions of this new system. Using standard Suzuki methodology, it was possible to prepare dicyclophanes bearing two octafluoro[2.2]paracyclophane units separated by both one and two benzene rings.
KW - Dicyclophane
KW - OFP
KW - Octafluoro[2.2]paracyclophane
KW - Paracyclophane
KW - Suzuki aryl cross-coupling
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U2 - https://doi.org/10.1016/j.jfluchem.2004.11.008
DO - https://doi.org/10.1016/j.jfluchem.2004.11.008
M3 - Article
VL - 126
SP - 481
EP - 488
JO - Journal of Fluorine Chemistry
JF - Journal of Fluorine Chemistry
SN - 0022-1139
IS - 4
ER -