Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes
Publication type: Journal Article
Publication date: 2021-05-13
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
33983038
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
We report the gold-catalyzed reaction of vinyldiazo compounds and alkenylsilanes to produce skipped dienes, which are common structural motifs in an array of bioactive compounds. This carbon-carbon bond-forming transformation proceeds with complete regio- and stereoselectivity with the silyl group serving as a regio- and stereocontrolling element. Likewise, the use of alkynylsilanes as reaction partners yielded skipped enynes resulting from a C(sp)-C(sp3) coupling. Mechanistic experiments and DFT studies have provided support for a stepwise mechanism.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
|
|
|
ACS Catalysis
2 publications, 14.29%
|
|
|
Chemistry - A European Journal
1 publication, 7.14%
|
|
|
Angewandte Chemie - International Edition
1 publication, 7.14%
|
|
|
Angewandte Chemie
1 publication, 7.14%
|
|
|
Synfacts
1 publication, 7.14%
|
|
|
Organic Letters
1 publication, 7.14%
|
|
|
Chemical Science
1 publication, 7.14%
|
|
|
Chemistry - An Asian Journal
1 publication, 7.14%
|
|
|
Synthesis
1 publication, 7.14%
|
|
|
Asian Journal of Organic Chemistry
1 publication, 7.14%
|
|
|
Russian Chemical Reviews
1 publication, 7.14%
|
|
|
Catalysis Science and Technology
1 publication, 7.14%
|
|
|
Organic and Biomolecular Chemistry
1 publication, 7.14%
|
|
|
1
2
|
Publishers
|
1
2
3
4
5
|
|
|
Wiley
5 publications, 35.71%
|
|
|
American Chemical Society (ACS)
3 publications, 21.43%
|
|
|
Royal Society of Chemistry (RSC)
3 publications, 21.43%
|
|
|
Georg Thieme Verlag KG
2 publications, 14.29%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 7.14%
|
|
|
1
2
3
4
5
|
- 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
14
Total citations:
14
Citations from 2024:
6
(42.86%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Bernardo O. et al. Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes // Organic Letters. 2021. Vol. 23. No. 11. pp. 4452-4456.
GOST all authors (up to 50)
Copy
Bernardo O., Yamamoto K., Fernandez I., López L. A. Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes // Organic Letters. 2021. Vol. 23. No. 11. pp. 4452-4456.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.1c01381
UR - https://doi.org/10.1021/acs.orglett.1c01381
TI - Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes
T2 - Organic Letters
AU - Bernardo, Olaya
AU - Yamamoto, Kota
AU - Fernandez, Israel
AU - López, L. A.
PY - 2021
DA - 2021/05/13
PB - American Chemical Society (ACS)
SP - 4452-4456
IS - 11
VL - 23
PMID - 33983038
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2021_Bernardo,
author = {Olaya Bernardo and Kota Yamamoto and Israel Fernandez and L. A. López},
title = {Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes},
journal = {Organic Letters},
year = {2021},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.orglett.1c01381},
number = {11},
pages = {4452--4456},
doi = {10.1021/acs.orglett.1c01381}
}
Cite this
MLA
Copy
Bernardo, Olaya, et al. “Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes.” Organic Letters, vol. 23, no. 11, May. 2021, pp. 4452-4456. https://doi.org/10.1021/acs.orglett.1c01381.