Abstract
By mediation of samarium diiodide and hexamethylphosphoramide, benzaldehydes and acetophenones underwent self- and cross-couplings to give the products having linkages at the para-carbons of phenyl rings and the carbonyl groups. The phenyl-carbonyl coupling of 2,5-dimethoxybenzaldehyde generated a Sm(III)-enolate intermediate, which was trapped by alkyl halides in a stereospecific manner to give uncommon 1,4-dialkyl-2,5-cyclohexadiene-1-carboxaldehydes. The benzaldehydes bearing tethered carbonyl chains proceeded with intramolecular phenyl-carbonyl couplings to afford fused benzocycles.
| Original language | English |
|---|---|
| Pages (from-to) | 4643-4649 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 62 |
| Issue number | 14 |
| DOIs | |
| Publication status | Published - 1997 Jan 1 |
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All Science Journal Classification (ASJC) codes
- Organic Chemistry
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Phenyl-Carbonyl Coupling Reactions Promoted by Samarium Diiodide and Hexamethylphosphoramide. / Shiue, Jiann Shyng; Lin, Mei-Huey; Fang, Jim Min.
In: Journal of Organic Chemistry, Vol. 62, No. 14, 01.01.1997, p. 4643-4649.Research output: Contribution to journal › Article
TY - JOUR
T1 - Phenyl-Carbonyl Coupling Reactions Promoted by Samarium Diiodide and Hexamethylphosphoramide
AU - Shiue, Jiann Shyng
AU - Lin, Mei-Huey
AU - Fang, Jim Min
PY - 1997/1/1
Y1 - 1997/1/1
N2 - By mediation of samarium diiodide and hexamethylphosphoramide, benzaldehydes and acetophenones underwent self- and cross-couplings to give the products having linkages at the para-carbons of phenyl rings and the carbonyl groups. The phenyl-carbonyl coupling of 2,5-dimethoxybenzaldehyde generated a Sm(III)-enolate intermediate, which was trapped by alkyl halides in a stereospecific manner to give uncommon 1,4-dialkyl-2,5-cyclohexadiene-1-carboxaldehydes. The benzaldehydes bearing tethered carbonyl chains proceeded with intramolecular phenyl-carbonyl couplings to afford fused benzocycles.
AB - By mediation of samarium diiodide and hexamethylphosphoramide, benzaldehydes and acetophenones underwent self- and cross-couplings to give the products having linkages at the para-carbons of phenyl rings and the carbonyl groups. The phenyl-carbonyl coupling of 2,5-dimethoxybenzaldehyde generated a Sm(III)-enolate intermediate, which was trapped by alkyl halides in a stereospecific manner to give uncommon 1,4-dialkyl-2,5-cyclohexadiene-1-carboxaldehydes. The benzaldehydes bearing tethered carbonyl chains proceeded with intramolecular phenyl-carbonyl couplings to afford fused benzocycles.
UR - http://www.scopus.com/inward/record.url?scp=0001200434&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0001200434&partnerID=8YFLogxK
U2 - 10.1021/jo9702498
DO - 10.1021/jo9702498
M3 - Article
VL - 62
SP - 4643
EP - 4649
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 14
ER -