Abstract
(Matrix presented) Palladium(0)-catalyzed cross-coupling reactions between tris(dihydropyranyl)indium 1 and aryl halides 2 have been investigated. Aryl iodides and electron-deficient aryl bromides couple efficiently with the in situ-generated indium reagents in the presence of 1-5 mol % Cl 2Pd(PPh3)2 to produce substituted dihydropyrans 3 with minimal (<10%) dimer (4) formation. Organoindium reagents derived from D-glucal also undergo cross couplings with aryl iodides to produce C-aryl glycals.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 2405-2408 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 5 |
| Issue number | 14 |
| DOIs | |
| State | Published - Jul 10 2003 |
| Externally published | Yes |
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- Molecular Medicine
Cite this
Palladium-catalyzed cross-coupling reactions between dihydropyranylindium reagents and aryl halides. Synthesis of C-aryl glycals. / Lehmann, Ute; Awasthi, Smita; Minehan, Thomas.
In: Organic Letters, Vol. 5, No. 14, 10.07.2003, p. 2405-2408.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Palladium-catalyzed cross-coupling reactions between dihydropyranylindium reagents and aryl halides. Synthesis of C-aryl glycals
AU - Lehmann, Ute
AU - Awasthi, Smita
AU - Minehan, Thomas
PY - 2003/7/10
Y1 - 2003/7/10
N2 - (Matrix presented) Palladium(0)-catalyzed cross-coupling reactions between tris(dihydropyranyl)indium 1 and aryl halides 2 have been investigated. Aryl iodides and electron-deficient aryl bromides couple efficiently with the in situ-generated indium reagents in the presence of 1-5 mol % Cl 2Pd(PPh3)2 to produce substituted dihydropyrans 3 with minimal (<10%) dimer (4) formation. Organoindium reagents derived from D-glucal also undergo cross couplings with aryl iodides to produce C-aryl glycals.
AB - (Matrix presented) Palladium(0)-catalyzed cross-coupling reactions between tris(dihydropyranyl)indium 1 and aryl halides 2 have been investigated. Aryl iodides and electron-deficient aryl bromides couple efficiently with the in situ-generated indium reagents in the presence of 1-5 mol % Cl 2Pd(PPh3)2 to produce substituted dihydropyrans 3 with minimal (<10%) dimer (4) formation. Organoindium reagents derived from D-glucal also undergo cross couplings with aryl iodides to produce C-aryl glycals.
UR - http://www.scopus.com/inward/record.url?scp=0141854965&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0141854965&partnerID=8YFLogxK
U2 - 10.1021/ol0345428
DO - 10.1021/ol0345428
M3 - Article
C2 - 12841741
AN - SCOPUS:0141854965
VL - 5
SP - 2405
EP - 2408
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 14
ER -