TY - JOUR
T1 - DFT Studies on the Mechanism of the Iridium-Catalyzed Formal [4 + 1] Cycloaddition of Biphenylene with Alkenes
AU - Takano, Hideaki
AU - Sugimura, Natsuhiko
AU - Kanyiva, Kyalo Stephen
AU - Shibata, Takanori
N1 - Funding Information:
This work was supported by JST, ACT-C, Japan, and Waseda University Grant for Special Research Projects. We would like to thank Prof. Ken Sakata (Hoshi University) for helpful discussions. All of the calculations were performed at The Materials Characterization Central Laboratory of Waseda University: an open-end laboratory program for fourth-year undergraduate and graduate students.18 We are grateful to Umicore for generous supports in [IrCl(cod)]2 supply.
Publisher Copyright:
© 2017 American Chemical Society.
Copyright:
Copyright 2021 Elsevier B.V., All rights reserved.
PY - 2017/8/31
Y1 - 2017/8/31
N2 - Recently, we reported an Ir-catalyzed formal [4 + 1] cycloaddition of biphenylenes with alkenes, which gave 9,9-disubstituted fluorenes in moderate to excellent yields. We proposed a reaction mechanism that involved the intermolecular insertion of alkenes, β-elimination, and intramolecular insertion based on the results of experimental mechanistic studies. Herein, we further support the proposed mechanism by density functional theory calculations and explain why [4 + 1] cycloaddition proceeds rather than conventional [4 + 2] cycloaddition.
AB - Recently, we reported an Ir-catalyzed formal [4 + 1] cycloaddition of biphenylenes with alkenes, which gave 9,9-disubstituted fluorenes in moderate to excellent yields. We proposed a reaction mechanism that involved the intermolecular insertion of alkenes, β-elimination, and intramolecular insertion based on the results of experimental mechanistic studies. Herein, we further support the proposed mechanism by density functional theory calculations and explain why [4 + 1] cycloaddition proceeds rather than conventional [4 + 2] cycloaddition.
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U2 - 10.1021/acsomega.7b00403
DO - 10.1021/acsomega.7b00403
M3 - Article
AN - SCOPUS:85054502748
VL - 2
SP - 5228
EP - 5234
JO - ACS Omega
JF - ACS Omega
SN - 2470-1343
IS - 8
ER -