TY - JOUR
T1 - Iridium-Catalyzed Formal [4 + 1] Cycloaddition of Biphenylenes with Alkenes Initiated by C-C Bond Cleavage for the Synthesis of 9,9-Disubstituted Fluorenes
AU - Takano, Hideaki
AU - Kanyiva, Kyalo Stephen
AU - Shibata, Takanori
N1 - Funding Information:
This work was supported by ACT-C from JST (Japan).
Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/4/15
Y1 - 2016/4/15
N2 - An Ir-catalyzed intermolecular reaction of biphenylenes as a C4 unit with various alkenes as a C1 unit gave 9,9-disubstituted fluorenes in moderate to high yields. Preliminary mechanistic studies revealed that this formal [4 + 1] cycloaddition probably proceeds via C-C bond cleavage, alkene insertion, β-hydrogen elimination, intramolecular alkene insertion, and then reductive elimination. An example of enantioselective reaction was also disclosed.
AB - An Ir-catalyzed intermolecular reaction of biphenylenes as a C4 unit with various alkenes as a C1 unit gave 9,9-disubstituted fluorenes in moderate to high yields. Preliminary mechanistic studies revealed that this formal [4 + 1] cycloaddition probably proceeds via C-C bond cleavage, alkene insertion, β-hydrogen elimination, intramolecular alkene insertion, and then reductive elimination. An example of enantioselective reaction was also disclosed.
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U2 - 10.1021/acs.orglett.6b00619
DO - 10.1021/acs.orglett.6b00619
M3 - Article
AN - SCOPUS:84966378444
SN - 1523-7060
VL - 18
SP - 1860
EP - 1863
JO - Organic Letters
JF - Organic Letters
IS - 8
ER -