volume 24 issue 2 pages 692-696

Palladium-Catalyzed Silylation of 2,3-Allenols with Unactivated Disilanes: Access to 2-Silyl-1,3-butadienes and α-Silyl-β-hydroxy Vinylsilanes

Publication typeJournal Article
Publication date2022-01-04
scimago Q1
wos Q1
SJR1.235
CiteScore8.7
Impact factor5.0
ISSN15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Regioselective silylation of 2,3-allenols with disilanes was carried out under catalysis of Pd2dba3/P(o-MeOC6H4)3. In the presence of Cs2CO3, the reaction achieved 2-silyl-1,3-dienes. Reaction of 1-aryl-2,3-allenols gave the products with excellent Z/E selectivity and E-isomers as the major species. Reaction of α-alkylallenols or α-alkyl-α-aryl-allenols resulted in products with moderate Z/E selectivity and E-isomers are also major. Without a base, the reaction produced α-silyl-β-hydroxyl vinylsilanes, which were converted to 2-silyl-1,3-dienes upon treatment with Cs2CO3.
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Xu G., Wang Z. Palladium-Catalyzed Silylation of 2,3-Allenols with Unactivated Disilanes: Access to 2-Silyl-1,3-butadienes and α-Silyl-β-hydroxy Vinylsilanes // Organic Letters. 2022. Vol. 24. No. 2. pp. 692-696.
GOST all authors (up to 50) Copy
Xu G., Wang Z. Palladium-Catalyzed Silylation of 2,3-Allenols with Unactivated Disilanes: Access to 2-Silyl-1,3-butadienes and α-Silyl-β-hydroxy Vinylsilanes // Organic Letters. 2022. Vol. 24. No. 2. pp. 692-696.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.1c04141
UR - https://doi.org/10.1021/acs.orglett.1c04141
TI - Palladium-Catalyzed Silylation of 2,3-Allenols with Unactivated Disilanes: Access to 2-Silyl-1,3-butadienes and α-Silyl-β-hydroxy Vinylsilanes
T2 - Organic Letters
AU - Xu, Guang-Li
AU - Wang, Zhong-Xia
PY - 2022
DA - 2022/01/04
PB - American Chemical Society (ACS)
SP - 692-696
IS - 2
VL - 24
PMID - 35057630
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Xu,
author = {Guang-Li Xu and Zhong-Xia Wang},
title = {Palladium-Catalyzed Silylation of 2,3-Allenols with Unactivated Disilanes: Access to 2-Silyl-1,3-butadienes and α-Silyl-β-hydroxy Vinylsilanes},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acs.orglett.1c04141},
number = {2},
pages = {692--696},
doi = {10.1021/acs.orglett.1c04141}
}
MLA
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MLA Copy
Xu, Guang-Li, et al. “Palladium-Catalyzed Silylation of 2,3-Allenols with Unactivated Disilanes: Access to 2-Silyl-1,3-butadienes and α-Silyl-β-hydroxy Vinylsilanes.” Organic Letters, vol. 24, no. 2, Jan. 2022, pp. 692-696. https://doi.org/10.1021/acs.orglett.1c04141.