Synthesis of α-Vinyltrialkoxysilanes via Nickel-Mediated Cross-Electrophile Coupling Reactions
Publication type: Journal Article
Publication date: 2023-10-16
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
37844143
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Vinyltrialkoxysilanes are indispensable for organic synthesis, particularly cross-coupling reactions. Hydrosilylation of alkynes inevitably yields α- and β-isomers of vinyltrialkoxysilanes even with complex ligands and catalysts, limiting its usage in organic synthesis. We report the synthesis of α-vinyltrialkoxysilanes via cross-electrophile C(sp2)–C(sp2) coupling of bromoalkenes. The method is quite compatible with functional groups under milder reaction conditions. The gram-scale synthesis of most substrates is impressive. The intermediacy of vinyl iodide and radical escape rebound path are supported by mechanistic studies.
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Chindan B. et al. Synthesis of α-Vinyltrialkoxysilanes via Nickel-Mediated Cross-Electrophile Coupling Reactions // Organic Letters. 2023. Vol. 25. No. 42. pp. 7751-7756.
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Chindan B., Syam A., Mahendran H., Rasappan R. Synthesis of α-Vinyltrialkoxysilanes via Nickel-Mediated Cross-Electrophile Coupling Reactions // Organic Letters. 2023. Vol. 25. No. 42. pp. 7751-7756.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.3c03206
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c03206
TI - Synthesis of α-Vinyltrialkoxysilanes via Nickel-Mediated Cross-Electrophile Coupling Reactions
T2 - Organic Letters
AU - Chindan, Bincy
AU - Syam, Anagha
AU - Mahendran, Hariharan
AU - Rasappan, Ramesh
PY - 2023
DA - 2023/10/16
PB - American Chemical Society (ACS)
SP - 7751-7756
IS - 42
VL - 25
PMID - 37844143
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2023_Chindan,
author = {Bincy Chindan and Anagha Syam and Hariharan Mahendran and Ramesh Rasappan},
title = {Synthesis of α-Vinyltrialkoxysilanes via Nickel-Mediated Cross-Electrophile Coupling Reactions},
journal = {Organic Letters},
year = {2023},
volume = {25},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.3c03206},
number = {42},
pages = {7751--7756},
doi = {10.1021/acs.orglett.3c03206}
}
Cite this
MLA
Copy
Chindan, Bincy, et al. “Synthesis of α-Vinyltrialkoxysilanes via Nickel-Mediated Cross-Electrophile Coupling Reactions.” Organic Letters, vol. 25, no. 42, Oct. 2023, pp. 7751-7756. https://pubs.acs.org/doi/10.1021/acs.orglett.3c03206.