New catalytic system for S-S and Se-Se bond addition to alkynes based on phosphite ligands
Publication type: Journal Article
Publication date: 2005-02-15
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 new catalytic system for the Ar2E2 (E = S, Se) addition to terminal alkynes (HC⋮C−R) has been developed to synthesize bis-element-substituted alkenes Z-H(ArE)CC(EAr)R with high stereoselectivity and yields. Utilizing phosphite ligand P(OiPr)3 allowed solving two major problems of this catalytic reaction: (1) prevent catalyst polymerization and (2) simplify product purification procedures. Key intermediatestrans-[Pd(SPh)2(P(OiPr)3)2] and trans-[Pd2(SPh)4(P(OiPr)3)2]were synthesized by S−S oxidative addition reaction to Pd(0) and studied by X-ray analysis. The equilibrium between the mononuclear and dinuclear complexes in solution was established by 31P NMR spectroscopy. In addition to the advantages in the synthetic procedure, the isolation of the stable palladium complexes with phosphite ligand made possible a detailed mechanistic study of the catalytic reaction.
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GOST
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Ananikov V. P. et al. New catalytic system for S-S and Se-Se bond addition to alkynes based on phosphite ligands // Organometallics. 2005. Vol. 24. No. 6. pp. 1275-1283.
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Ananikov V. P., Kabeshov M. A., Beletskaya I. P., Khrustalev V. N., Antipin M. Y. New catalytic system for S-S and Se-Se bond addition to alkynes based on phosphite ligands // Organometallics. 2005. Vol. 24. No. 6. pp. 1275-1283.
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TY - JOUR
DO - 10.1021/om049082g
UR - https://doi.org/10.1021/om049082g
TI - New catalytic system for S-S and Se-Se bond addition to alkynes based on phosphite ligands
T2 - Organometallics
AU - Ananikov, Valentine P.
AU - Kabeshov, Michael A
AU - Beletskaya, Irina P.
AU - Khrustalev, Vicktor N
AU - Antipin, Mikhail Yu.
PY - 2005
DA - 2005/02/15
PB - American Chemical Society (ACS)
SP - 1275-1283
IS - 6
VL - 24
SN - 0276-7333
SN - 1520-6041
ER -
Cite this
BibTex (up to 50 authors)
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@article{2005_Ananikov,
author = {Valentine P. Ananikov and Michael A Kabeshov and Irina P. Beletskaya and Vicktor N Khrustalev and Mikhail Yu. Antipin},
title = {New catalytic system for S-S and Se-Se bond addition to alkynes based on phosphite ligands},
journal = {Organometallics},
year = {2005},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/om049082g},
number = {6},
pages = {1275--1283},
doi = {10.1021/om049082g}
}
Cite this
MLA
Copy
Ananikov, Valentine P., et al. “New catalytic system for S-S and Se-Se bond addition to alkynes based on phosphite ligands.” Organometallics, vol. 24, no. 6, Feb. 2005, pp. 1275-1283. https://doi.org/10.1021/om049082g.
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