(Z)- or (E)-Selective hydrogenation of potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate: route to either isomer of β-trifluoromethylstyrenes.
Publication type: Journal Article
Publication date: 2015-02-23
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
25705923
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A Pd-catalyzed hydrogenation of potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate providing either the (Z)- or (E)-isomer of the vinylborate in >98% purity is described. The initially formed (Z)-isomer of the alkene is transformed to the (E)-isomer with time, irrespective of the catalyst used; coupling with bromo- and iodoarenes provides a variety of (Z)- or (E)-β-trifluoromethylstyrenes. Also, a safe synthesis of the alkynyltrifluoroborate from HFC-245fa and BF3·OEt2 has been described.
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Total citations:
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Ramachandran P. V., Mitsuhashi W. (Z)- or (E)-Selective hydrogenation of potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate: route to either isomer of β-trifluoromethylstyrenes. // Organic Letters. 2015. Vol. 17. No. 5. pp. 1252-1255.
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Ramachandran P. V., Mitsuhashi W. (Z)- or (E)-Selective hydrogenation of potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate: route to either isomer of β-trifluoromethylstyrenes. // Organic Letters. 2015. Vol. 17. No. 5. pp. 1252-1255.
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TY - JOUR
DO - 10.1021/acs.orglett.5b00235
UR - https://doi.org/10.1021/acs.orglett.5b00235
TI - (Z)- or (E)-Selective hydrogenation of potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate: route to either isomer of β-trifluoromethylstyrenes.
T2 - Organic Letters
AU - Ramachandran, P Veeraraghavan
AU - Mitsuhashi, Wataru
PY - 2015
DA - 2015/02/23
PB - American Chemical Society (ACS)
SP - 1252-1255
IS - 5
VL - 17
PMID - 25705923
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2015_Ramachandran,
author = {P Veeraraghavan Ramachandran and Wataru Mitsuhashi},
title = {(Z)- or (E)-Selective hydrogenation of potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate: route to either isomer of β-trifluoromethylstyrenes.},
journal = {Organic Letters},
year = {2015},
volume = {17},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acs.orglett.5b00235},
number = {5},
pages = {1252--1255},
doi = {10.1021/acs.orglett.5b00235}
}
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Ramachandran, P. Veeraraghavan, and Wataru Mitsuhashi. “(Z)- or (E)-Selective hydrogenation of potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate: route to either isomer of β-trifluoromethylstyrenes..” Organic Letters, vol. 17, no. 5, Feb. 2015, pp. 1252-1255. https://doi.org/10.1021/acs.orglett.5b00235.