Homogeneous nickel catalysts for the selective transfer of a single arylthio group in the catalytic hydrothiolation of alkynes
Publication type: Journal Article
Publication date: 2006-08-12
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
A novel homogeneous catalytic system has been developed for the regioselective hydrothiolation of alkynes based on CpNi(NHC)Cl complexes (NHC = N-heterocyclic carbene). The designed catalyst was efficient for the selective addition of a single ArS group to an alkyne and was suitable for the synthesis of vinylsulfides, without side reactions leading to bis(arylthio)alkenes. Furthermore, this catalytic system allowed for the S−H bond addition to alkynes to be performed with high regioselectivity (up to 31:1) and in good yields (61−87%). A mechanistic study showed that this reaction involved three steps: (1) a nickel-based substitution of chloride for the ArS group, (2) alkyne insertion into the Ni−S bond, and (3) protonolysis of the Ni−C bond. The intermediate CpNi(NHC)(SAr) complexes were unambiguously characterized by X-ray analysis.
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GOST
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Malyshev D. A. et al. Homogeneous nickel catalysts for the selective transfer of a single arylthio group in the catalytic hydrothiolation of alkynes // Organometallics. 2006. Vol. 25. No. 19. pp. 4462-4470.
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Malyshev D. A., Scott N. M., Marion N., Stevens E. D., Ananikov V. P., Beletskaya I. P., Nolan S. P. Homogeneous nickel catalysts for the selective transfer of a single arylthio group in the catalytic hydrothiolation of alkynes // Organometallics. 2006. Vol. 25. No. 19. pp. 4462-4470.
Cite this
RIS
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TY - JOUR
DO - 10.1021/om060302v
UR - https://doi.org/10.1021/om060302v
TI - Homogeneous nickel catalysts for the selective transfer of a single arylthio group in the catalytic hydrothiolation of alkynes
T2 - Organometallics
AU - Malyshev, Denis A
AU - Scott, Natalie M.
AU - Marion, Nicolas
AU - Stevens, Edwin D.
AU - Ananikov, Valentine P.
AU - Beletskaya, Irina P.
AU - Nolan, Steven P.
PY - 2006
DA - 2006/08/12
PB - American Chemical Society (ACS)
SP - 4462-4470
IS - 19
VL - 25
SN - 0276-7333
SN - 1520-6041
ER -
Cite this
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@article{2006_Malyshev,
author = {Denis A Malyshev and Natalie M. Scott and Nicolas Marion and Edwin D. Stevens and Valentine P. Ananikov and Irina P. Beletskaya and Steven P. Nolan},
title = {Homogeneous nickel catalysts for the selective transfer of a single arylthio group in the catalytic hydrothiolation of alkynes},
journal = {Organometallics},
year = {2006},
volume = {25},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/om060302v},
number = {19},
pages = {4462--4470},
doi = {10.1021/om060302v}
}
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MLA
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Malyshev, Denis A., et al. “Homogeneous nickel catalysts for the selective transfer of a single arylthio group in the catalytic hydrothiolation of alkynes.” Organometallics, vol. 25, no. 19, Aug. 2006, pp. 4462-4470. https://doi.org/10.1021/om060302v.
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