Ligand-Controlled On–Off Switch of a Silicon-Tethered Directing Group Enabling the Regiodivergent Hydroalkylation of Vinylsilanes under Ni–H Catalysis
Publication type: Journal Article
Publication date: 2023-12-05
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
38051157
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A regiodivergent Ni–H-catalyzed hydroalkylation of vinylsilanes is described. Depending on the ancillary ligand at the nickel catalyst, the regioselectivity can be steered by a directing group attached to the silicon atom. The mild protocols allow for the selective synthesis of either branched or linear alkylsilanes. An example of a vinylgermane is also reported. The method features a broad scope with high functional-group tolerance and follows a radical mechanism.
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Brösamlen D., Oestreich M. Ligand-Controlled On–Off Switch of a Silicon-Tethered Directing Group Enabling the Regiodivergent Hydroalkylation of Vinylsilanes under Ni–H Catalysis // Organic Letters. 2023. Vol. 26. No. 5. pp. 977-982.
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Brösamlen D., Oestreich M. Ligand-Controlled On–Off Switch of a Silicon-Tethered Directing Group Enabling the Regiodivergent Hydroalkylation of Vinylsilanes under Ni–H Catalysis // Organic Letters. 2023. Vol. 26. No. 5. pp. 977-982.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.3c03799
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c03799
TI - Ligand-Controlled On–Off Switch of a Silicon-Tethered Directing Group Enabling the Regiodivergent Hydroalkylation of Vinylsilanes under Ni–H Catalysis
T2 - Organic Letters
AU - Brösamlen, Daniel
AU - Oestreich, Martin
PY - 2023
DA - 2023/12/05
PB - American Chemical Society (ACS)
SP - 977-982
IS - 5
VL - 26
PMID - 38051157
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2023_Brösamlen,
author = {Daniel Brösamlen and Martin Oestreich},
title = {Ligand-Controlled On–Off Switch of a Silicon-Tethered Directing Group Enabling the Regiodivergent Hydroalkylation of Vinylsilanes under Ni–H Catalysis},
journal = {Organic Letters},
year = {2023},
volume = {26},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.3c03799},
number = {5},
pages = {977--982},
doi = {10.1021/acs.orglett.3c03799}
}
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MLA
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Brösamlen, Daniel, and Martin Oestreich. “Ligand-Controlled On–Off Switch of a Silicon-Tethered Directing Group Enabling the Regiodivergent Hydroalkylation of Vinylsilanes under Ni–H Catalysis.” Organic Letters, vol. 26, no. 5, Dec. 2023, pp. 977-982. https://pubs.acs.org/doi/10.1021/acs.orglett.3c03799.
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