B-N, B-O, and B-CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes.
Rafal M Dziedzic
1
,
Liban M A Saleh
1
,
Jonathan Axtell
1
,
Joshua L Martin
1
,
Simone L Stevens
1
,
A. Timothy Royappa
2, 3
,
Arnold L. Rheingold
2
,
Alexander M Spokoyny
1
3
Department
of Chemistry, University of West Florida, 11000 University Parkway, Pensacola, Florida 32514, United States
|
Publication type: Journal Article
Publication date: 2016-07-13
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
27384544
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Carboranes are boron-rich molecules that can be functionalized through metal-catalyzed cross-coupling. Here, for the first time, we report the use of bromo-carboranes in palladium-catalyzed cross-coupling for efficient B-N, B-O, and unprecedented B-CN bond formation. In many cases bromo-carboranes outperform the traditionally utilized iodo-carborane species. This marked difference in reactivity is leveraged to circumvent multistep functionalization by directly coupling small nucleophiles (-OH, -NH2, and -CN) and multiple functional groups onto the boron-rich clusters.
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Metrics
115
Total citations:
115
Citations from 2024:
17
(14.79%)
Cite this
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MLA
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GOST
Copy
Dziedzic R. M. et al. B-N, B-O, and B-CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes. // Journal of the American Chemical Society. 2016. Vol. 138. No. 29. pp. 9081-9084.
GOST all authors (up to 50)
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Dziedzic R. M., Saleh L. M. A., Axtell J., Martin J. L., Stevens S. L., Royappa A. T., Rheingold A. L., Spokoyny A. M. B-N, B-O, and B-CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes. // Journal of the American Chemical Society. 2016. Vol. 138. No. 29. pp. 9081-9084.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jacs.6b05505
UR - https://doi.org/10.1021/jacs.6b05505
TI - B-N, B-O, and B-CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes.
T2 - Journal of the American Chemical Society
AU - Dziedzic, Rafal M
AU - Saleh, Liban M A
AU - Axtell, Jonathan
AU - Martin, Joshua L
AU - Stevens, Simone L
AU - Royappa, A. Timothy
AU - Rheingold, Arnold L.
AU - Spokoyny, Alexander M
PY - 2016
DA - 2016/07/13
PB - American Chemical Society (ACS)
SP - 9081-9084
IS - 29
VL - 138
PMID - 27384544
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2016_Dziedzic,
author = {Rafal M Dziedzic and Liban M A Saleh and Jonathan Axtell and Joshua L Martin and Simone L Stevens and A. Timothy Royappa and Arnold L. Rheingold and Alexander M Spokoyny},
title = {B-N, B-O, and B-CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes.},
journal = {Journal of the American Chemical Society},
year = {2016},
volume = {138},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/jacs.6b05505},
number = {29},
pages = {9081--9084},
doi = {10.1021/jacs.6b05505}
}
Cite this
MLA
Copy
Dziedzic, Rafal M., et al. “B-N, B-O, and B-CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes..” Journal of the American Chemical Society, vol. 138, no. 29, Jul. 2016, pp. 9081-9084. https://doi.org/10.1021/jacs.6b05505.