Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 5228-5234 |
| Number of pages | 7 |
| Journal | ACS Omega |
| Volume | 2 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 2017 Jan 1 |
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ASJC Scopus subject areas
- Chemistry(all)
- Chemical Engineering(all)
Cite this
DFT Studies on the Mechanism of the Iridium-Catalyzed Formal [4 + 1] Cycloaddition of Biphenylene with Alkenes. / Takano, Hideaki; Sugimura, Natsuhiko; Kanyiva, Stephen Kyalo; Shibata, Takanori.
In: ACS Omega, Vol. 2, No. 8, 01.01.2017, p. 5228-5234.Research output: Contribution to journal › Article
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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, Stephen Kyalo
AU - Shibata, Takanori
PY - 2017/1/1
Y1 - 2017/1/1
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.
UR - http://www.scopus.com/inward/record.url?scp=85054502748&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85054502748&partnerID=8YFLogxK
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 -