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Synlett
Volumn , Issue 10, 2008, Pages 1529-1531
Direct one-pot synthesis of 2,3-diarylbuta-1,3-diene via self-coupling of acetophenones
Author keywords

2,3 diarylbuta 1,3 diene; Acetophenone; Self coupling
Indexed keywords

1,3 BUTADIENE; ACETOPHENONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SAMARIUM;
EID: 46449089033     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/S-2008-1078412     Document Type: Article
Times cited : (6)
References (32)
  • 31
    • 46449086644 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of 2,3-Diarylbuta-1,3-dienes (Method A): To the stirred acetophenone or its analogues 1 (1 mmol) in an oven-dried glassware under a nitrogen atmosphere, samarium diiodide (1 mmol) in THF (15 mL) was added dropwise. Generally the reaction finished within 15 min. After the deep blue color faded, Ac2O (1.2 mmol) was added to the yellow mixture rapidly. The reaction mixture was stirred under reflux until reaction completion. After the usual workup, the crude product was purified by silica gel column chromatography using EtOAc-PE (1:20) as eluent to afford the corresponding pure buta-1,3-diene2.
    • General Procedure for the Synthesis of 2,3-Diarylbuta-1,3-dienes (Method A): To the stirred acetophenone or its analogues 1 (1 mmol) in an oven-dried glassware under a nitrogen atmosphere, samarium diiodide (1 mmol) in THF (15 mL) was added dropwise. Generally the reaction finished within 15 min. After the deep blue color faded, Ac2O (1.2 mmol) was added to the yellow mixture rapidly. The reaction mixture was stirred under reflux until reaction completion. After the usual workup, the crude product was purified by silica gel column chromatography using EtOAc-PE (1:20) as eluent to afford the corresponding pure buta-1,3-diene2.
  • 32
    • 46449105403 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of 2,3-Bis(4-bromophenyl)buta-1,3- diene and 2,3-Bis(4-chloro-phenyl)buta-1,3-diene (Method B): To the stirred 4-chloro- or 4-bromo-substituted acetophenone (1 mmol) in an oven-dried glassware under a nitrogen atmosphere, samarium diiodide (1 mmol) in THF (15 mL) was added dropwise. Generally the reaction finished within 15 min. After the deep blue color faded, THF was removed under reduced pressure, then MeCN (3 mL) and Ac2O (3.0 mmol) were added to the yellow mixture successively, and the resulting mixture was stirred under reflux until reaction completion. After the usual workup, the crude product was purified by silica gel column chromatography using EtOAc-PE (1:20) as eluent to afford the corresponding diene.
    • General Procedure for the Synthesis of 2,3-Bis(4-bromophenyl)buta-1,3- diene and 2,3-Bis(4-chloro-phenyl)buta-1,3-diene (Method B): To the stirred 4-chloro- or 4-bromo-substituted acetophenone (1 mmol) in an oven-dried glassware under a nitrogen atmosphere, samarium diiodide (1 mmol) in THF (15 mL) was added dropwise. Generally the reaction finished within 15 min. After the deep blue color faded, THF was removed under reduced pressure, then MeCN (3 mL) and Ac2O (3.0 mmol) were added to the yellow mixture successively, and the resulting mixture was stirred under reflux until reaction completion. After the usual workup, the crude product was purified by silica gel column chromatography using EtOAc-PE (1:20) as eluent to afford the corresponding diene.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.