Abstract
The operationally simple palladium-catalyzed double-bond migration without heteroatom-containing coordinating functional groups is described. Addition of TaCl 5 as a second catalyst greatly enhanced the migration efficiency to provide β-alkylstyrenes through migration of up to a five-carbon chain. Both catalysts were commercially available, and the reaction occurred without external ligands under neutral conditions. The reaction proceeded via generation of π-allyl palladium species, which enabled the chemoselective double-bond migration of hydrocarbons in the presence of allylethers. Remote functionalization through double-bond migration was also demonstrated using FeCl 3 as a second catalyst.
| Original language | English |
|---|---|
| Pages (from-to) | 2769-2772 |
| Number of pages | 4 |
| Journal | Chemical Communications |
| Volume | 55 |
| Issue number | 19 |
| DOIs | |
| Publication status | Published - Jan 1 2019 |
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ASJC Scopus subject areas
- Catalysis
- Electronic, Optical and Magnetic Materials
- Ceramics and Composites
- Chemistry(all)
- Surfaces, Coatings and Films
- Metals and Alloys
- Materials Chemistry
Cite this
Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride. / Murai, Masahito; Nishimura, Kengo; Takai, Kazuhiko.
In: Chemical Communications, Vol. 55, No. 19, 01.01.2019, p. 2769-2772.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride
AU - Murai, Masahito
AU - Nishimura, Kengo
AU - Takai, Kazuhiko
PY - 2019/1/1
Y1 - 2019/1/1
N2 - The operationally simple palladium-catalyzed double-bond migration without heteroatom-containing coordinating functional groups is described. Addition of TaCl 5 as a second catalyst greatly enhanced the migration efficiency to provide β-alkylstyrenes through migration of up to a five-carbon chain. Both catalysts were commercially available, and the reaction occurred without external ligands under neutral conditions. The reaction proceeded via generation of π-allyl palladium species, which enabled the chemoselective double-bond migration of hydrocarbons in the presence of allylethers. Remote functionalization through double-bond migration was also demonstrated using FeCl 3 as a second catalyst.
AB - The operationally simple palladium-catalyzed double-bond migration without heteroatom-containing coordinating functional groups is described. Addition of TaCl 5 as a second catalyst greatly enhanced the migration efficiency to provide β-alkylstyrenes through migration of up to a five-carbon chain. Both catalysts were commercially available, and the reaction occurred without external ligands under neutral conditions. The reaction proceeded via generation of π-allyl palladium species, which enabled the chemoselective double-bond migration of hydrocarbons in the presence of allylethers. Remote functionalization through double-bond migration was also demonstrated using FeCl 3 as a second catalyst.
UR - http://www.scopus.com/inward/record.url?scp=85062371548&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85062371548&partnerID=8YFLogxK
U2 - 10.1039/c9cc00223e
DO - 10.1039/c9cc00223e
M3 - Article
C2 - 30768079
AN - SCOPUS:85062371548
VL - 55
SP - 2769
EP - 2772
JO - Chemical Communications
JF - Chemical Communications
SN - 1359-7345
IS - 19
ER -