C−C Bond Formation via C−H Bond Activation: Catalytic Arylation and Alkenylation of Alkane Segments
Publication type: Journal Article
Publication date: 2002-10-16
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
12418875
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
A new system for catalytic arylation and alkenylation of alkane segments has been developed. The ortho-tert-butylaniline substrates and 2-pivaloylpyridine may be arylated and alkenylated at the tert-butyl group, while no functionalization occurred at more reactive C-H and other bonds. Arylation and alkenylation of these substrates are achieved in the presence of Ph2Si(OH)Me and Ph-CH=CH-Si(OH)Me2, respectively, and the catalytic amount of Pd(OAc)2 and stoichiometric oxidant (Cu(OAc)2, 2 equiv) in DMF. In contrast, the ortho-i-propylaniline substrate underwent cyclopalladation, but no arylation product was obtained. Complex compound 14 was synthesized via tandem arylation-alkenylation of tert-butylaniline 11. We hypothesize that the high selectivity of this system stems from the confluence of directing effect of the Schiff base or pyridine moiety and unique reactivity properties of a phenyl-palladium acetate species (Ph-Pd-OAc.Ln).
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GOST
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Sezen B., Franz R., Sames D. C−C Bond Formation via C−H Bond Activation: Catalytic Arylation and Alkenylation of Alkane Segments // Journal of the American Chemical Society. 2002. Vol. 124. No. 45. pp. 13372-13373.
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Sezen B., Franz R., Sames D. C−C Bond Formation via C−H Bond Activation: Catalytic Arylation and Alkenylation of Alkane Segments // Journal of the American Chemical Society. 2002. Vol. 124. No. 45. pp. 13372-13373.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ja027891q
UR - https://doi.org/10.1021/ja027891q
TI - C−C Bond Formation via C−H Bond Activation: Catalytic Arylation and Alkenylation of Alkane Segments
T2 - Journal of the American Chemical Society
AU - Sezen, Bengü
AU - Franz, Roberto
AU - Sames, Dalibor
PY - 2002
DA - 2002/10/16
PB - American Chemical Society (ACS)
SP - 13372-13373
IS - 45
VL - 124
PMID - 12418875
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
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@article{2002_Sezen,
author = {Bengü Sezen and Roberto Franz and Dalibor Sames},
title = {C−C Bond Formation via C−H Bond Activation: Catalytic Arylation and Alkenylation of Alkane Segments},
journal = {Journal of the American Chemical Society},
year = {2002},
volume = {124},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/ja027891q},
number = {45},
pages = {13372--13373},
doi = {10.1021/ja027891q}
}
Cite this
MLA
Copy
Sezen, Bengü, et al. “C−C Bond Formation via C−H Bond Activation: Catalytic Arylation and Alkenylation of Alkane Segments.” Journal of the American Chemical Society, vol. 124, no. 45, Oct. 2002, pp. 13372-13373. https://doi.org/10.1021/ja027891q.