Double elimination protocol for the synthesis of arylene ethynylenes containing heteroaromatic rings

2005 ◽  
Vol 83 (6-7) ◽  
pp. 716-727 ◽  
Author(s):  
Akihiro Orita ◽  
Fangguo Ye ◽  
Govindarajulu Babu ◽  
Tomohiro Ikemoto ◽  
Junzo Otera
Keyword(s):  
Aldol Reaction ◽  
Phenylene Ethynylene ◽  
Elimination Reaction ◽  
One Pot

The double elimination reaction of β-substituted sulfones offers a versatile strategy for synthesis of arylene ethynylene kits containing heteroaromatic rings. A sequence of aldol reaction between α-sulfonyl carbanion and aldehyde, trapping the resulting aldolate to give β-substituted sulfone, and double elimination of this intermediate can be integrated in one pot. This protocol allows thiophene, pyridine, and ferrocene units to be accommodated in phenylene ethynylene arrays.Key words: arylene–ethynylenes, heteroaromatic rings, ferrocene, double elimination, sulfones.

Double elimination protocol for aryleneethynylenes

2006 ◽  
Vol 78 (4) ◽  
pp. 731-748 ◽  
Author(s):  
Junzo Otera
Keyword(s):  
Aldol Reaction ◽  
Aromatic Aldehydes ◽  
Elimination Reaction ◽  
One Pot ◽  
Acetylenic Bond ◽  
Leaving Group

A variety of aryleneethynylenes are synthesized by double elimination reaction of β-substituted sulfones. The acetylenic bond is formed from readily available aromatic aldehydes and benzylic sulfones. A sequence of aldol reaction, trapping of the aldolates with a leaving group, and eliminations proceeds in one pot. The utility of this protocol is exemplified by synthesis of dihalo diphenylacetylenes, 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene, and double-helical aromatic acetylenes.

Studies on the synthesis of 2-acyl-1H-indenes via one-pot palladium-catalysed tandem Heck–aldol reaction

2010 ◽  
Vol 2010 (5) ◽  
pp. 254-258 ◽  
Author(s):  
Song Tu ◽  
Yong Sha ◽  
Long-He Xu ◽  
Zong-Yuan Xiao ◽  
Li-Yi Ye ◽  
...  
Keyword(s):  
Aldol Reaction ◽  
One Pot

Convenient Synthesis of (1-Propynyl)arenes through a One-Pot Double Elimination Reaction, and Their Conversion to Enynes

Synlett ◽  
2007 ◽  
Vol 2007 (12) ◽  
pp. 1909-1912 ◽  
Author(s):  
De-Lie An ◽  
Akihiro Orita ◽  
Junzo Otera ◽  
Zhiyang Zhang ◽  
Hidetaka Mineyama
Keyword(s):  
Elimination Reaction ◽  
One Pot ◽  
Convenient Synthesis

One-Pot Approach for C-C Bond Formation through Ruthenium-Amido Complex Catalyzed Tandem Aldol Reaction/Hydrogenation

Synthesis ◽  
2010 ◽  
Vol 2010 (15) ◽  
pp. 2577-2582 ◽  
Author(s):  
Hong Liu ◽  
Haifeng Sun ◽  
Deju Ye ◽  
Hualiang Jiang ◽  
Kaixian Chen
Keyword(s):  
Bond Formation ◽  
Aldol Reaction ◽  
One Pot

One-Pot Approach to Chiral Chromenes via Enantioselective Organocatalytic Domino Oxa-Michael—Aldol Reaction.

ChemInform ◽  
2007 ◽  
Vol 38 (21) ◽  
Author(s):  
Hao Li ◽  
Jian Wang ◽  
Timiyin E-Nunu ◽  
Liansuo Zu ◽  
Wei Jiang ◽  
...  
Keyword(s):  
Aldol Reaction ◽  
One Pot
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