A Convenient Method for the Generation of Allylic Dihaloboranes and Diallyl(chloro)borane and Their Application in the Allylboration of Alkenes and Acetylenes
Publication type: Journal Article
Publication date: 2005-11-01
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
A convenient approach to the highly reactive allylic dihaloboranes and diallyl(chloro)borane based on exchange reactions between BHal3 (Hal = Cl, Br) and allylic triorganoboranes (allyl, cinnamyl and 2-methylenecyclobutane derivatives) has been developed. The compounds thus generated readily react with terminal alkenes and acetylenes to form the corresponding cis-1,2-allylboration products. These products were isolated by standard techniques and transformed into boronates (boron amides). Deboronation of these products led to 1,4-pentadiene derivatives or unsaturated alcohols. 2-Substituted 1,4-pentadienyl(dichloro)boranes obtained from acetylenes underwent intramolecular chloroboration at a moderate temperature to form 5-chloro-2-borinene derivatives. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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Total citations:
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Citations from 2024:
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GOST
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Bubnov Y. N. et al. A Convenient Method for the Generation of Allylic Dihaloboranes and Diallyl(chloro)borane and Their Application in the Allylboration of Alkenes and Acetylenes // European Journal of Organic Chemistry. 2005. Vol. 2005. No. 21. pp. 4633-4639.
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Bubnov Y. N., Kuznetsov N. Y., Pastukhov F. V., Kublitsky V. V. A Convenient Method for the Generation of Allylic Dihaloboranes and Diallyl(chloro)borane and Their Application in the Allylboration of Alkenes and Acetylenes // European Journal of Organic Chemistry. 2005. Vol. 2005. No. 21. pp. 4633-4639.
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RIS
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TY - JOUR
DO - 10.1002/ejoc.200500391
UR - https://doi.org/10.1002/ejoc.200500391
TI - A Convenient Method for the Generation of Allylic Dihaloboranes and Diallyl(chloro)borane and Their Application in the Allylboration of Alkenes and Acetylenes
T2 - European Journal of Organic Chemistry
AU - Bubnov, Yuri N
AU - Kuznetsov, Nikolai Yu.
AU - Pastukhov, Fedor V
AU - Kublitsky, Vadim V
PY - 2005
DA - 2005/11/01
PB - Wiley
SP - 4633-4639
IS - 21
VL - 2005
SN - 1434-193X
SN - 1099-0690
ER -
Cite this
BibTex (up to 50 authors)
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@article{2005_Bubnov,
author = {Yuri N Bubnov and Nikolai Yu. Kuznetsov and Fedor V Pastukhov and Vadim V Kublitsky},
title = {A Convenient Method for the Generation of Allylic Dihaloboranes and Diallyl(chloro)borane and Their Application in the Allylboration of Alkenes and Acetylenes},
journal = {European Journal of Organic Chemistry},
year = {2005},
volume = {2005},
publisher = {Wiley},
month = {nov},
url = {https://doi.org/10.1002/ejoc.200500391},
number = {21},
pages = {4633--4639},
doi = {10.1002/ejoc.200500391}
}
Cite this
MLA
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Bubnov, Yuri N., et al. “A Convenient Method for the Generation of Allylic Dihaloboranes and Diallyl(chloro)borane and Their Application in the Allylboration of Alkenes and Acetylenes.” European Journal of Organic Chemistry, vol. 2005, no. 21, Nov. 2005, pp. 4633-4639. https://doi.org/10.1002/ejoc.200500391.