Role of the Base in Buchwald–Hartwig Amination
2
Pharmaceutical
Development, Global Medicines Development, AstraZeneca, Pepparedsleden 1, SE-431 83 Mölndal, Sweden
|
Publication type: Journal Article
Publication date: 2014-11-04
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
25340530
Organic Chemistry
Abstract
The Buchwald-Hartwig amination has been investigated theoretically and experimentally to examine the scope of possible bases under different reaction conditions. Nonpolar solvents resist the formation of new charges. Therefore, the base should be anionic to be able to deprotonate the neutral palladium-amine complex and/or expel the anionic leaving group (bromide). The calculated barrier for the organic base DBU was found to be prohibitively high. In polar solvent, dissociation of bromide becomes possible, but here the base will instead form a complex with palladium, creating an overly stable resting state. The conclusions for both solvent classes hold for both a hindered monodentate phosphine and the labile bidentate ligand BINAP. The computational studies were supported by experimental testing of a range of bases using BINAP in two different solvents, toluene and DMF.
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94
Total citations:
94
Citations from 2024:
22
(23.4%)
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GOST
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Sunesson Y. et al. Role of the Base in Buchwald–Hartwig Amination // Journal of Organic Chemistry. 2014. Vol. 79. No. 24. pp. 11961-11969.
GOST all authors (up to 50)
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Sunesson Y., Limé E., O. Nilsson Lill S., Meadows R. E., Norrby P. Role of the Base in Buchwald–Hartwig Amination // Journal of Organic Chemistry. 2014. Vol. 79. No. 24. pp. 11961-11969.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo501817m
UR - https://doi.org/10.1021/jo501817m
TI - Role of the Base in Buchwald–Hartwig Amination
T2 - Journal of Organic Chemistry
AU - Sunesson, Ylva
AU - Limé, Elaine
AU - O. Nilsson Lill, Sten
AU - Meadows, Rebecca E
AU - Norrby, Per-Ola
PY - 2014
DA - 2014/11/04
PB - American Chemical Society (ACS)
SP - 11961-11969
IS - 24
VL - 79
PMID - 25340530
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2014_Sunesson,
author = {Ylva Sunesson and Elaine Limé and Sten O. Nilsson Lill and Rebecca E Meadows and Per-Ola Norrby},
title = {Role of the Base in Buchwald–Hartwig Amination},
journal = {Journal of Organic Chemistry},
year = {2014},
volume = {79},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/jo501817m},
number = {24},
pages = {11961--11969},
doi = {10.1021/jo501817m}
}
Cite this
MLA
Copy
Sunesson, Ylva, et al. “Role of the Base in Buchwald–Hartwig Amination.” Journal of Organic Chemistry, vol. 79, no. 24, Nov. 2014, pp. 11961-11969. https://doi.org/10.1021/jo501817m.