Abstract
We developed a copper-catalyzed 5-position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives. The reaction proceeded with high functional group tolerance under mild conditions. In the case of quinolines with an amide, carbamate, urea, or sulfonamide group at the 8-position of quinoline moieties, a radical scavenger experiment indicated that the reaction proceeded via a radical pathway. The protecting group of an 8-amidoquinoline derivative could be removed by hydrolysis. On the other hand, the trifluoromethylation of 8-aminoquinolines was also promoted by other Lewis acids as well as a copper catalyst and proceeded even in the presence of a radical scavenger. These results indicated that the trifluoromethylation of 8-aminoquinolines proceeded via a Friedel-Crafts-type reaction. Interestingly, the copper salt works as either a catalyst for the formation of a CF3 radical or a Lewis acid to promote a Friedel-Crafts-type reaction, depending on the substrate.
| Original language | English |
|---|---|
| Pages (from-to) | 8092-8100 |
| Number of pages | 9 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 14 |
| Issue number | 34 |
| DOIs | |
| Publication status | Published - Jan 1 2016 |
| Externally published | Yes |
Fingerprint
All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
5-Position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives. / Kuninobu, Yoichiro; Nishi, Mitsumi; Kanai, Motomu.
In: Organic and Biomolecular Chemistry, Vol. 14, No. 34, 01.01.2016, p. 8092-8100.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - 5-Position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives
AU - Kuninobu, Yoichiro
AU - Nishi, Mitsumi
AU - Kanai, Motomu
PY - 2016/1/1
Y1 - 2016/1/1
N2 - We developed a copper-catalyzed 5-position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives. The reaction proceeded with high functional group tolerance under mild conditions. In the case of quinolines with an amide, carbamate, urea, or sulfonamide group at the 8-position of quinoline moieties, a radical scavenger experiment indicated that the reaction proceeded via a radical pathway. The protecting group of an 8-amidoquinoline derivative could be removed by hydrolysis. On the other hand, the trifluoromethylation of 8-aminoquinolines was also promoted by other Lewis acids as well as a copper catalyst and proceeded even in the presence of a radical scavenger. These results indicated that the trifluoromethylation of 8-aminoquinolines proceeded via a Friedel-Crafts-type reaction. Interestingly, the copper salt works as either a catalyst for the formation of a CF3 radical or a Lewis acid to promote a Friedel-Crafts-type reaction, depending on the substrate.
AB - We developed a copper-catalyzed 5-position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives. The reaction proceeded with high functional group tolerance under mild conditions. In the case of quinolines with an amide, carbamate, urea, or sulfonamide group at the 8-position of quinoline moieties, a radical scavenger experiment indicated that the reaction proceeded via a radical pathway. The protecting group of an 8-amidoquinoline derivative could be removed by hydrolysis. On the other hand, the trifluoromethylation of 8-aminoquinolines was also promoted by other Lewis acids as well as a copper catalyst and proceeded even in the presence of a radical scavenger. These results indicated that the trifluoromethylation of 8-aminoquinolines proceeded via a Friedel-Crafts-type reaction. Interestingly, the copper salt works as either a catalyst for the formation of a CF3 radical or a Lewis acid to promote a Friedel-Crafts-type reaction, depending on the substrate.
UR - http://www.scopus.com/inward/record.url?scp=84984661272&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84984661272&partnerID=8YFLogxK
U2 - 10.1039/c6ob01325b
DO - 10.1039/c6ob01325b
M3 - Article
AN - SCOPUS:84984661272
VL - 14
SP - 8092
EP - 8100
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 34
ER -