Abstract
An efficient, direct synthesis of pyrazolo-[5,1-a]isoindoles employing a palladium-catalyzed intramolecular C-H bond activation of 1-(2-halobenzyl) pyrazoles has been developed. The use of lithium chloride (LiCl) was found to be essential in these reactions, to suppress further C-H bond activation at the C-3 position of pyrazolo[5,1-a]isoindole, when C-3 is unsubstituted. This protocol can be applied to the synthesis of a pyrazolo[5,1-a]isoquinoline possessing a six-membered central ring system and a fully substituted pyrazolo[5,1-a]isoindole using sequential intra- and intermolecular C-H bond activation.
| Original language | English |
|---|---|
| Pages (from-to) | 2041-2049 |
| Number of pages | 9 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 352 |
| Issue number | 11-12 |
| DOIs | |
| Publication status | Published - 2010 Sep 13 |
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Keywords
- C-H activation
- Direct arylation
- Palladium
- Pyrazoles
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
Cite this
Direct synthesis of pyrazolo[5,1-a]isoindoles via intramolecular palladium-catalyzed C-H bond activation. / Choi, Young Lok; Lee, Hyuk; Kim, Bum Tae; Choi, Kihang; Heo, Jung Nyoung.
In: Advanced Synthesis and Catalysis, Vol. 352, No. 11-12, 13.09.2010, p. 2041-2049.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Direct synthesis of pyrazolo[5,1-a]isoindoles via intramolecular palladium-catalyzed C-H bond activation
AU - Choi, Young Lok
AU - Lee, Hyuk
AU - Kim, Bum Tae
AU - Choi, Kihang
AU - Heo, Jung Nyoung
PY - 2010/9/13
Y1 - 2010/9/13
N2 - An efficient, direct synthesis of pyrazolo-[5,1-a]isoindoles employing a palladium-catalyzed intramolecular C-H bond activation of 1-(2-halobenzyl) pyrazoles has been developed. The use of lithium chloride (LiCl) was found to be essential in these reactions, to suppress further C-H bond activation at the C-3 position of pyrazolo[5,1-a]isoindole, when C-3 is unsubstituted. This protocol can be applied to the synthesis of a pyrazolo[5,1-a]isoquinoline possessing a six-membered central ring system and a fully substituted pyrazolo[5,1-a]isoindole using sequential intra- and intermolecular C-H bond activation.
AB - An efficient, direct synthesis of pyrazolo-[5,1-a]isoindoles employing a palladium-catalyzed intramolecular C-H bond activation of 1-(2-halobenzyl) pyrazoles has been developed. The use of lithium chloride (LiCl) was found to be essential in these reactions, to suppress further C-H bond activation at the C-3 position of pyrazolo[5,1-a]isoindole, when C-3 is unsubstituted. This protocol can be applied to the synthesis of a pyrazolo[5,1-a]isoquinoline possessing a six-membered central ring system and a fully substituted pyrazolo[5,1-a]isoindole using sequential intra- and intermolecular C-H bond activation.
KW - C-H activation
KW - Direct arylation
KW - Palladium
KW - Pyrazoles
UR - http://www.scopus.com/inward/record.url?scp=77956378879&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77956378879&partnerID=8YFLogxK
U2 - 10.1002/adsc.201000260
DO - 10.1002/adsc.201000260
M3 - Article
AN - SCOPUS:77956378879
VL - 352
SP - 2041
EP - 2049
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 11-12
ER -