A nickel-catalyzed carbozincation of aryl-substituted alkynes
Publication type: Journal Article
Publication date: 1998-02-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Abstract The addition of dialkylzincs or diphenylzinc to substituted phenylacetylenes in the presence of catalytic amounts of Ni(acac)2 in THF : NMP mixtures produces syn-carbozincation products with good to excellent regio- and stereoselectivity. After quenching with an electrophile (iodine, acyl chloride, allyl bromide) tetrasubstituted olefines are obtained in good to satisfactory yields. An intramolecular version of the reaction is possible using a terminal triple bond bearing an iodine at a remote position. More substituted iodo-alkynes furnish only reductive elimination products. An application to a stereoselective synthesis of (Z)-tamoxifen (Z : E>99 : 1) has been developed.
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Total citations:
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GOST
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Stüdemann T., Ibrahim-Ouali M., Knochel P. A nickel-catalyzed carbozincation of aryl-substituted alkynes // Tetrahedron. 1998. Vol. 54. No. 7. pp. 1299-1316.
GOST all authors (up to 50)
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Stüdemann T., Ibrahim-Ouali M., Knochel P. A nickel-catalyzed carbozincation of aryl-substituted alkynes // Tetrahedron. 1998. Vol. 54. No. 7. pp. 1299-1316.
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RIS
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TY - JOUR
DO - 10.1016/S0040-4020(97)10226-5
UR - https://doi.org/10.1016/S0040-4020(97)10226-5
TI - A nickel-catalyzed carbozincation of aryl-substituted alkynes
T2 - Tetrahedron
AU - Stüdemann, Thomas
AU - Ibrahim-Ouali, Malika
AU - Knochel, Paul
PY - 1998
DA - 1998/02/01
PB - Elsevier
SP - 1299-1316
IS - 7
VL - 54
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{1998_Stüdemann,
author = {Thomas Stüdemann and Malika Ibrahim-Ouali and Paul Knochel},
title = {A nickel-catalyzed carbozincation of aryl-substituted alkynes},
journal = {Tetrahedron},
year = {1998},
volume = {54},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/S0040-4020(97)10226-5},
number = {7},
pages = {1299--1316},
doi = {10.1016/S0040-4020(97)10226-5}
}
Cite this
MLA
Copy
Stüdemann, Thomas, et al. “A nickel-catalyzed carbozincation of aryl-substituted alkynes.” Tetrahedron, vol. 54, no. 7, Feb. 1998, pp. 1299-1316. https://doi.org/10.1016/S0040-4020(97)10226-5.