Reaction of aluminacyclopentadienes with aldehydes affording cyclopentadiene derivatives

Fang, Hongyun; Zhao, Chengchun; Li, Guotao; Xi, Zhenfeng

doi:10.1016/s0040-4020(03)00522-2

Cited by 34 publications

(15 citation statements)

References 50 publications

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“…Their reactions with aldehydes at room temperature give cyclopentadiene derivatives including tetrahydroindenes in good to excellent yields [77].…”

Section: Scheme 19mentioning

confidence: 99%

Recent developments in homobimetallic reagents and catalysts for organic synthesis

Shimeng

et al. 2011

Chin. Sci. Bull.

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Organometallics are a family of useful organic chemicals because they play important roles in organic synthesis as reagents and as catalysts. They can be classified according to the number of metals they contain. Bimetallic compounds are important organometallics and they are either homobimetallic or heterobimetallic depending on whether the two metals are the same or different. In this paper, we focus on homobimetallic compounds. Homobimetallic compounds are generally used as dianions to react with electrophiles in organic synthesis. Recently, homobimetallics have also been used as catalysts in organic reactions such as in asymmetric reactions. homobimetallics, reagent, catalyst, synthesis, application Citation:Wu W, Gu D L, Wang S M, et al. Recent developments in homobimetallic reagents and catalysts for organic synthesis.

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“…Their reactions with aldehydes at room temperature give cyclopentadiene derivatives including tetrahydroindenes in good to excellent yields [77].…”

Section: Scheme 19mentioning

confidence: 99%

Recent developments in homobimetallic reagents and catalysts for organic synthesis

Shimeng

et al. 2011

Chin. Sci. Bull.

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“…Reaction of 9 with aldehydes afforded multiply substituted cyclopentadienes [21]. Deoxygenation of carbonyl groups took place in these reactions.…”

Section: Reaction Of Aluminacyclopentadienes With Aldehydes Affordingmentioning

confidence: 99%

New Methods for the Preparation of Multiply Substituted Cyclopentadienes and Related Compounds

2005

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Substituents on cyclopentadienyl ligands significantly influence the reactivity and catalytic efficiency of their transition metal complexes. Therefore, development of synthetic methods for cyclopentadiene derivatives possessing different substituents has been in great demand. In this paper, we report new synthetic methods for multiply substituted cyclopentadienes recently developed in this group. In principle, three types of preparative methods are described. Firstly, zirconacyclopentadienes in the presence of Lewis acids react with aldehydes to afford multiply substituted cyclopentadienes, thus providing a one-pot procedure from two molecules of identical or different alkynes and one molecule of aldehyde; reaction of aluminacyclopentadienes with aldehydes also result in high-yield formation of multiply substituted cyclopentadienes. Secondly, 1,2,3,4-tetrasubstituted 1,4-dilithio-and 1,4-bis(magnesiobromo)-1,3-diene derivatives react with aldehydes or ketones via deoxygenation of the C@O moieties to afford cyclopentadiene derivatives. Thirdly, monolithio reagents, 1,2,3,4-tetrasubstituted 1-lithio-1,3-butadienes, and Grignard reagents, 1,2,3,4-tetrasubstituted 1-magnesiobromo-1,3-butadienes react with aldehydes or ketones to afford cyclopentadiene derivatives upon hydrolysis.

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“…Much less has been reported previously about aluminum-substituted 1,3-dienes. Eisch [8] and Hoberg [9] reported the preparation of alumina-1,3-cyclopentadienes decades ago, but very little has been done with them synthetically [10].…”

Section: Introductionmentioning

confidence: 99%

Substituted Dienols from Palladium Catalyzed Coupling of Hydroaluminated Enynols with Aryl Iodides

Crook¹,

Nie²,

Welker

2008

LOC

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Reaction of aluminacyclopentadienes with aldehydes affording cyclopentadiene derivatives

Cited by 34 publications

References 50 publications

Recent developments in homobimetallic reagents and catalysts for organic synthesis

Recent developments in homobimetallic reagents and catalysts for organic synthesis

New Methods for the Preparation of Multiply Substituted Cyclopentadienes and Related Compounds

Substituted Dienols from Palladium Catalyzed Coupling of Hydroaluminated Enynols with Aryl Iodides

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