Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition
Publication type: Journal Article
Publication date: 2019-01-09
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
30624069
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Z-Selective synthesis of vinyl boronates is challenging. This work describes Fe-catalyzed addition of alkyl radicals, formed by the corresponding alkyl halides, to ethynyl ethynylboronic acid pinacol ester that gives rise to Z-vinyl boronates in high stereoselectivity. The method works best for tertiary and secondary alkyl iodides. The Z-vinyl boronate products are easily converted to other Z-alkenes by transformation of the boronate group. The method is applied for the formal total synthesis of a 5-HT2c receptor agonist.
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12
Total citations:
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Citations from 2024:
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(50%)
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GOST
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Barzanò G., Cheseaux A., Hu X. Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition // Organic Letters. 2019. Vol. 21. No. 2. pp. 490-493.
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Barzanò G., Cheseaux A., Hu X. Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition // Organic Letters. 2019. Vol. 21. No. 2. pp. 490-493.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.8b03772
UR - https://doi.org/10.1021/acs.orglett.8b03772
TI - Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition
T2 - Organic Letters
AU - Barzanò, Guido
AU - Cheseaux, Alexis
AU - Hu, Xile
PY - 2019
DA - 2019/01/09
PB - American Chemical Society (ACS)
SP - 490-493
IS - 2
VL - 21
PMID - 30624069
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2019_Barzanò,
author = {Guido Barzanò and Alexis Cheseaux and Xile Hu},
title = {Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition},
journal = {Organic Letters},
year = {2019},
volume = {21},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acs.orglett.8b03772},
number = {2},
pages = {490--493},
doi = {10.1021/acs.orglett.8b03772}
}
Cite this
MLA
Copy
Barzanò, Guido, et al. “Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition.” Organic Letters, vol. 21, no. 2, Jan. 2019, pp. 490-493. https://doi.org/10.1021/acs.orglett.8b03772.