Zirconium-catalyzed methylalumination of heterosubstituted arylethynes: Factors affecting the regio-, stereo-, and chemoselectivities
Publication type: Journal Article
Publication date: 2007-10-01
scimago Q3
wos Q2
SJR: 0.385
CiteScore: 4.1
Impact factor: 2.4
ISSN: 0022328X, 18728561
PubMed ID:
19746204
Materials Chemistry
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The Zr-catalyzed methylalumination of heterosubstituted arylethynes containing O, S, Cl, and Si can proceed in high yields (>70%) and in a highly regio- and stereoselective manner (≥98-99%), although SO(2)Ph, Br, and Cl in a benzylic position present serious chemoselectivity-related problems. The low regioselectivity of 60% initially observed with o-ethynylphenol (1a) has been elevated to ≥98% through the use of either a catalytic amount of Zr(ebi)Cl(2) or Zr(2-Me-Ind)(2)Cl(2) or, more conveniently, the stoichiometric amount of ZrCp(2)Cl(2), ZrCp(2)MeCl, or ZrCp(2)Me(2) in conjunction with the use of a deficient amount (0.9 molar equivalent) of I(2) for subsequent iodinolysis.
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Total citations:
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GOST
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Wang G., Zhu G., Negishi E. Zirconium-catalyzed methylalumination of heterosubstituted arylethynes: Factors affecting the regio-, stereo-, and chemoselectivities // Journal of Organometallic Chemistry. 2007. Vol. 692. No. 21. pp. 4731-4736.
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Wang G., Zhu G., Negishi E. Zirconium-catalyzed methylalumination of heterosubstituted arylethynes: Factors affecting the regio-, stereo-, and chemoselectivities // Journal of Organometallic Chemistry. 2007. Vol. 692. No. 21. pp. 4731-4736.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/j.jorganchem.2007.05.052
UR - https://doi.org/10.1016/j.jorganchem.2007.05.052
TI - Zirconium-catalyzed methylalumination of heterosubstituted arylethynes: Factors affecting the regio-, stereo-, and chemoselectivities
T2 - Journal of Organometallic Chemistry
AU - Wang, Guangwei
AU - Zhu, Gangguo
AU - Negishi, Ei-ichi
PY - 2007
DA - 2007/10/01
PB - Elsevier
SP - 4731-4736
IS - 21
VL - 692
PMID - 19746204
SN - 0022-328X
SN - 1872-8561
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2007_Wang,
author = {Guangwei Wang and Gangguo Zhu and Ei-ichi Negishi},
title = {Zirconium-catalyzed methylalumination of heterosubstituted arylethynes: Factors affecting the regio-, stereo-, and chemoselectivities},
journal = {Journal of Organometallic Chemistry},
year = {2007},
volume = {692},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/j.jorganchem.2007.05.052},
number = {21},
pages = {4731--4736},
doi = {10.1016/j.jorganchem.2007.05.052}
}
Cite this
MLA
Copy
Wang, Guangwei, et al. “Zirconium-catalyzed methylalumination of heterosubstituted arylethynes: Factors affecting the regio-, stereo-, and chemoselectivities.” Journal of Organometallic Chemistry, vol. 692, no. 21, Oct. 2007, pp. 4731-4736. https://doi.org/10.1016/j.jorganchem.2007.05.052.