Abstract
Sequential formation of distant bonds in organic molecules was achieved for the palladium-catalyzed hydrosilylation/cyclization of various 1,n-dienes by chain walking of the metal catalyst. The reaction was applicable to various 1,n-dienes, including a 1,13-diene, to form a cyclopentane ring as well as a carbon–silicon bond at a remote site. The use of “nondissociative” chain walking provides a fascinating strategy in organic synthesis to functionalize distant parts of organic molecules, in a particular order, within a catalytic cycle by effectively moving the reactive center from a remote position.
| Original language | English |
|---|---|
| Pages (from-to) | 5261-5265 |
| Number of pages | 5 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 58 |
| Issue number | 16 |
| DOIs | |
| Publication status | Published - 2019 Apr 8 |
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Keywords
- alkenes
- cyclizations
- hydrosilylation
- isomerizations
- palladium
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
Cite this
Metal-Catalyzed Sequential Formation of Distant Bonds in Organic Molecules : Palladium-Catalyzed Hydrosilylation/Cyclization of 1,n-Dienes by Chain Walking. / Kochi, Takuya; Ichinose, Kazuya; Shigekane, Masayuki; Hamasaki, Taro; Kakiuchi, Fumitoshi.
In: Angewandte Chemie - International Edition, Vol. 58, No. 16, 08.04.2019, p. 5261-5265.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Metal-Catalyzed Sequential Formation of Distant Bonds in Organic Molecules
T2 - Palladium-Catalyzed Hydrosilylation/Cyclization of 1,n-Dienes by Chain Walking
AU - Kochi, Takuya
AU - Ichinose, Kazuya
AU - Shigekane, Masayuki
AU - Hamasaki, Taro
AU - Kakiuchi, Fumitoshi
PY - 2019/4/8
Y1 - 2019/4/8
N2 - Sequential formation of distant bonds in organic molecules was achieved for the palladium-catalyzed hydrosilylation/cyclization of various 1,n-dienes by chain walking of the metal catalyst. The reaction was applicable to various 1,n-dienes, including a 1,13-diene, to form a cyclopentane ring as well as a carbon–silicon bond at a remote site. The use of “nondissociative” chain walking provides a fascinating strategy in organic synthesis to functionalize distant parts of organic molecules, in a particular order, within a catalytic cycle by effectively moving the reactive center from a remote position.
AB - Sequential formation of distant bonds in organic molecules was achieved for the palladium-catalyzed hydrosilylation/cyclization of various 1,n-dienes by chain walking of the metal catalyst. The reaction was applicable to various 1,n-dienes, including a 1,13-diene, to form a cyclopentane ring as well as a carbon–silicon bond at a remote site. The use of “nondissociative” chain walking provides a fascinating strategy in organic synthesis to functionalize distant parts of organic molecules, in a particular order, within a catalytic cycle by effectively moving the reactive center from a remote position.
KW - alkenes
KW - cyclizations
KW - hydrosilylation
KW - isomerizations
KW - palladium
UR - http://www.scopus.com/inward/record.url?scp=85062818660&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85062818660&partnerID=8YFLogxK
U2 - 10.1002/anie.201814558
DO - 10.1002/anie.201814558
M3 - Article
C2 - 30748069
AN - SCOPUS:85062818660
VL - 58
SP - 5261
EP - 5265
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 16
ER -