Facile synthesis and palladium-catalyzed cross-coupling reactions of 2,3-bis(pinacolatoboryl)-1,3-butadiene.

Facile synthesis and palladium-catalyzed cross-coupling reactions of 2,3-bis(pinacolatoboryl)-1,3-butadiene. Research Abstract Details 

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Facile synthesis and palladium-catalyzed cross-coupling reactions of 2,3-bis(pinacolatoboryl)-1,3-butadiene. Abstract Text:

Masaki Shimizu,Takuya Kurahashi,Katsuhiro Shimono,Kei Tanaka,Ikuhiro Nagao,Shin-ichi Kiyomoto,Tamejiro Hiyama,Masaki Shimizu,Takuya Kurahashi,Katsuhiro Shimono,Kei Tanaka,Ikuhiro Nagao,Shin-ichi Kiyomoto,Tamejiro Hiyama,Masaki Shimizu,Takuya Kurahashi,Katsuhiro Shimono,Kei Tanaka,Ikuhiro Nagao,Shin-ichi Kiyomoto,Tamejiro Hiyama,

Treatment of 1,1-bis(pinacolatoboryl)ethene with an excess of 1-bromo-1-lithioethene gave 2,3-bis(pinacolatoboryl)-1,3-butadiene in high yield. Palladium-catalyzed cross-coupling of the resulting diborylbutadiene with aryl iodides took place smoothly in the presence of a catalytic amount of Pd(OAc)2/PPh3 and aqueous KOH to give 2,3-diaryl-1,3-butadienes in good yields. The coupling reaction with commercially available 4-acetoxyphenylmethyl chloride under the same conditions followed by hydrolysis of the acetyl groups gave anolignan B in a one-pot manner. A variety of [3]- to [6]dendralenes were synthesized by palladium-catalyzed coupling of the diene or 1,1-bis(pinacolato)borylethene with alkenyl or dienyl halides, respectively, in good yields.

Facile synthesis and palladium-catalyzed cross-coupling reactions of 2,3-bis(pinacolatoboryl)-1,3-butadiene. Publishing Authors By Initials

M Shimizu,T Kurahashi,K Shimono,K Tanaka,I Nagao,S Kiyomoto,T Hiyama,M Shimizu,T Kurahashi,K Shimono,K Tanaka,I Nagao,S Kiyomoto,T Hiyama,M Shimizu,T Kurahashi,K Shimono,K Tanaka,I Nagao,S Kiyomoto,T Hiyama,

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Facile synthesis and palladium-catalyzed cross-coupling reactions of 2,3-bis(pinacolatoboryl)-1,3-butadiene. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Chemistry, an Asian journal

VOLUME: 2

Page Numbers: 1400-8

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ISSN: 1861-471X

DAY: 5

MONTH: Nov

YEAR: 2007

Facile synthesis and palladium-catalyzed cross-coupling reactions of 2,3-bis(pinacolatoboryl)-1,3-butadiene. Information

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LANGUAGE: eng

NlmUniqueID: 101294643

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Grant and Affiliation Information for Facile synthesis and palladium-catalyzed cross-coupling reactions of 2,3-bis(pinacolatoboryl)-1,3-butadiene.

AFFILIATION: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Nishikyo-ku, Kyoto 615-8510, Japan. shimizu@npc05.kuic.kyoto-u.ac.jp

Country: Germany

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MEDLINETA: Chem Asian J

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