Aluminum-Catalyzed Cross-Coupling of Silylalkynes with Aliphatic C–F Bonds
Publication type: Journal Article
Publication date: 2017-03-28
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
28350470
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
We report the generation of aliphatic and benzylic acetylenes via reaction of primary, secondary, and tertiary aliphatic fluorides with various trimethylsilyl acetylides. These reactions are catalyzed by Al and B Lewis acids, most effectively by the extremely fluorophilic tris(pentafluorophenyl)alane, representing the first example of catalytic incorporation of alkynes into aliphatic C-F positions. The fluorophilicity of the catalysts gives rise to fluorine selectivity over other halogens, allowing orthogonal reactivity pathways.
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42
Total citations:
42
Citations from 2025:
5
(11.9%)
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MLA
Cite this
GOST
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Jaiswal A. K. et al. Aluminum-Catalyzed Cross-Coupling of Silylalkynes with Aliphatic C–F Bonds // Organic Letters. 2017. Vol. 19. No. 7. pp. 1934-1937.
GOST all authors (up to 50)
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Jaiswal A. K., Goh K. K. K., Sung S., Young R. Aluminum-Catalyzed Cross-Coupling of Silylalkynes with Aliphatic C–F Bonds // Organic Letters. 2017. Vol. 19. No. 7. pp. 1934-1937.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.7b00712
UR - https://doi.org/10.1021/acs.orglett.7b00712
TI - Aluminum-Catalyzed Cross-Coupling of Silylalkynes with Aliphatic C–F Bonds
T2 - Organic Letters
AU - Jaiswal, Amit K.
AU - Goh, Kelvin K K
AU - Sung, Simon
AU - Young, R. D.
PY - 2017
DA - 2017/03/28
PB - American Chemical Society (ACS)
SP - 1934-1937
IS - 7
VL - 19
PMID - 28350470
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2017_Jaiswal,
author = {Amit K. Jaiswal and Kelvin K K Goh and Simon Sung and R. D. Young},
title = {Aluminum-Catalyzed Cross-Coupling of Silylalkynes with Aliphatic C–F Bonds},
journal = {Organic Letters},
year = {2017},
volume = {19},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.orglett.7b00712},
number = {7},
pages = {1934--1937},
doi = {10.1021/acs.orglett.7b00712}
}
Cite this
MLA
Copy
Jaiswal, Amit K., et al. “Aluminum-Catalyzed Cross-Coupling of Silylalkynes with Aliphatic C–F Bonds.” Organic Letters, vol. 19, no. 7, Mar. 2017, pp. 1934-1937. https://doi.org/10.1021/acs.orglett.7b00712.