γ-Selective Allylation of (E)-Alkenylzinc Iodides Prepared by Reductive Coupling of Arylacetylenes with Alkyl Iodides
Publication type: Journal Article
Publication date: 2016-06-17
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
27285459
Organic Chemistry
Abstract
The first examples of Cu-catalyzed γ-selective allylic alkenylation using organozinc reagents are reported. (E)-Alkenylzinc iodides were prepared by Fe-catalyzed reductive coupling of terminal arylalkynes with alkyl iodides. In the presence of a copper catalyst, these reagents reacted with allylic bromides derived from Morita-Baylis-Hillman alcohols to give 1,4-dienes in high yields. The reactions are highly γ-selective (generally γ/α > 49:1) and tolerate a wide range of functional groups such as ester, cyano, keto, and nitro.
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GOST
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Zhurkin F. E., Hu X. γ-Selective Allylation of (E)-Alkenylzinc Iodides Prepared by Reductive Coupling of Arylacetylenes with Alkyl Iodides // Journal of Organic Chemistry. 2016. Vol. 81. No. 13. pp. 5795-5802.
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Zhurkin F. E., Hu X. γ-Selective Allylation of (E)-Alkenylzinc Iodides Prepared by Reductive Coupling of Arylacetylenes with Alkyl Iodides // Journal of Organic Chemistry. 2016. Vol. 81. No. 13. pp. 5795-5802.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.6b01306
UR - https://doi.org/10.1021/acs.joc.6b01306
TI - γ-Selective Allylation of (E)-Alkenylzinc Iodides Prepared by Reductive Coupling of Arylacetylenes with Alkyl Iodides
T2 - Journal of Organic Chemistry
AU - Zhurkin, Fedor E
AU - Hu, Xile
PY - 2016
DA - 2016/06/17
PB - American Chemical Society (ACS)
SP - 5795-5802
IS - 13
VL - 81
PMID - 27285459
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2016_Zhurkin,
author = {Fedor E Zhurkin and Xile Hu},
title = {γ-Selective Allylation of (E)-Alkenylzinc Iodides Prepared by Reductive Coupling of Arylacetylenes with Alkyl Iodides},
journal = {Journal of Organic Chemistry},
year = {2016},
volume = {81},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.joc.6b01306},
number = {13},
pages = {5795--5802},
doi = {10.1021/acs.joc.6b01306}
}
Cite this
MLA
Copy
Zhurkin, Fedor E., and Xile Hu. “γ-Selective Allylation of (E)-Alkenylzinc Iodides Prepared by Reductive Coupling of Arylacetylenes with Alkyl Iodides.” Journal of Organic Chemistry, vol. 81, no. 13, Jun. 2016, pp. 5795-5802. https://doi.org/10.1021/acs.joc.6b01306.