Regioselective Unsymmetrical Tetraallylation of C60 through Palladium Catalysis
Publication type: Journal Article
Publication date: 2009-10-02
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
19919157
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
A Pd-catalyzed tetraallylation of C(60) that selectively occurs with an unsymmetrical addition pattern has been established. Treatment of C(60) with CH(2)=CHCH(2)Cl, CH(2)=CHCH(2)SnBu(3), and PdCl(2)[P(OPh)(3)](2) in 1,2-Cl(2)C(6)H(4) at 50 degrees C afforded the tetraallylated fullerene in 74% yield with virtually complete regioselectivity. Mechanistic investigations showed that (i) tetraallylation proceeds through consecutive nucleophilic/electrophilic allylations [likely via a bis(pi-allyl)palladium intermediate] and (ii) both steric (for the first diallylation) and electronic (for the second diallylation) factors are responsible for the high regioselectivity.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
5
10
15
20
25
|
|
|
Organic Letters
22 publications, 26.19%
|
|
|
Journal of Organic Chemistry
14 publications, 16.67%
|
|
|
Chemical Communications
6 publications, 7.14%
|
|
|
Organic and Biomolecular Chemistry
5 publications, 5.95%
|
|
|
Organic Chemistry Frontiers
3 publications, 3.57%
|
|
|
Angewandte Chemie - International Edition
3 publications, 3.57%
|
|
|
Angewandte Chemie
3 publications, 3.57%
|
|
|
Tetrahedron Letters
2 publications, 2.38%
|
|
|
Journal of the American Chemical Society
2 publications, 2.38%
|
|
|
Chemical Science
2 publications, 2.38%
|
|
|
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
1 publication, 1.19%
|
|
|
Journal of Materials Research
1 publication, 1.19%
|
|
|
ChemistryOpen
1 publication, 1.19%
|
|
|
Advanced Synthesis and Catalysis
1 publication, 1.19%
|
|
|
Journal of Heterocyclic Chemistry
1 publication, 1.19%
|
|
|
Journal of Physical Organic Chemistry
1 publication, 1.19%
|
|
|
Advanced Materials
1 publication, 1.19%
|
|
|
Chemical Record
1 publication, 1.19%
|
|
|
Chemistry - A European Journal
1 publication, 1.19%
|
|
|
New Journal of Chemistry
1 publication, 1.19%
|
|
|
Pure and Applied Chemistry
1 publication, 1.19%
|
|
|
Research
1 publication, 1.19%
|
|
|
Topics in Organometallic Chemistry
1 publication, 1.19%
|
|
|
Chinese Journal of Chemistry
1 publication, 1.19%
|
|
|
Synlett
1 publication, 1.19%
|
|
|
Chirality
1 publication, 1.19%
|
|
|
Mendeleev Communications
1 publication, 1.19%
|
|
|
Tetrahedron
1 publication, 1.19%
|
|
|
5
10
15
20
25
|
Publishers
|
5
10
15
20
25
30
35
40
|
|
|
American Chemical Society (ACS)
38 publications, 45.24%
|
|
|
Royal Society of Chemistry (RSC)
17 publications, 20.24%
|
|
|
Wiley
17 publications, 20.24%
|
|
|
Elsevier
3 publications, 3.57%
|
|
|
Springer Nature
2 publications, 2.38%
|
|
|
The Society of Synthetic Organic Chemistry, Japan
1 publication, 1.19%
|
|
|
Walter de Gruyter
1 publication, 1.19%
|
|
|
American Association for the Advancement of Science (AAAS)
1 publication, 1.19%
|
|
|
Georg Thieme Verlag KG
1 publication, 1.19%
|
|
|
OOO Zhurnal "Mendeleevskie Soobshcheniya"
1 publication, 1.19%
|
|
|
5
10
15
20
25
30
35
40
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
84
Total citations:
84
Citations from 2025:
4
(4.76%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Nambo M. et al. Regioselective Unsymmetrical Tetraallylation of C60 through Palladium Catalysis // Journal of the American Chemical Society. 2009. Vol. 131. No. 42. pp. 15112-15113.
GOST all authors (up to 50)
Copy
Nambo M., Wakamiya A., YAMAGUCHI S., Itami K. Regioselective Unsymmetrical Tetraallylation of C60 through Palladium Catalysis // Journal of the American Chemical Society. 2009. Vol. 131. No. 42. pp. 15112-15113.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ja9071173
UR - https://doi.org/10.1021/ja9071173
TI - Regioselective Unsymmetrical Tetraallylation of C60 through Palladium Catalysis
T2 - Journal of the American Chemical Society
AU - Nambo, Masakazu
AU - Wakamiya, Atsushi
AU - YAMAGUCHI, Shigehiro
AU - Itami, Kenichiro
PY - 2009
DA - 2009/10/02
PB - American Chemical Society (ACS)
SP - 15112-15113
IS - 42
VL - 131
PMID - 19919157
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2009_Nambo,
author = {Masakazu Nambo and Atsushi Wakamiya and Shigehiro YAMAGUCHI and Kenichiro Itami},
title = {Regioselective Unsymmetrical Tetraallylation of C60 through Palladium Catalysis},
journal = {Journal of the American Chemical Society},
year = {2009},
volume = {131},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/ja9071173},
number = {42},
pages = {15112--15113},
doi = {10.1021/ja9071173}
}
Cite this
MLA
Copy
Nambo, Masakazu, et al. “Regioselective Unsymmetrical Tetraallylation of C60 through Palladium Catalysis.” Journal of the American Chemical Society, vol. 131, no. 42, Oct. 2009, pp. 15112-15113. https://doi.org/10.1021/ja9071173.