Compounds of Aluminum in Organic Synthesis

Zietz, Joseph R.; Robinson, Gene C.; Lindsay, Kara

doi:10.1016/b978-008046518-0.00102-1

Cited by 21 publications

(3 citation statements)

References 343 publications

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“…[4][5][6][7] Nevertheless, some examples of the uncatalyzed hydroalumination of alkenes have been reported, although typically these reactions require elevated temperatures. [8][9] In this Letter, we demonstrate that carbon-aluminum and hydrogen-aluminum bonds can add across the carbon-carbon double bonds of highly strained alkenes rapidly at room temperature. These reactions, which proceed without a catalyst, occur with complete regiochemical and stereochemical control.…”

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confidence: 85%

Carboalumination of Seven-Membered-Ring trans-Alkenes

et al. 2020

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Seven-membered-ring trans-alkenes undergo rapid hydro-and carboalumination reactions in the absence of a catalyst with complete regio-and diastereoselectivity. Control experiments, including deuterium labeling, adding radical inhibitors, and using a radical clock, suggest that these reactions proceed by a concerted mechanism. The products of the reaction possess a new carbonaluminum bond that can then undergo subsequent transformations, particularly oxidation, providing functionalized products as single stereoisomers.

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confidence: 85%

Carboalumination of Seven-Membered-Ring trans-Alkenes

et al. 2020

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“…When tricoordinate aluminum reagents have C–H bonds β to the aluminum atom, as is the case for triisobutylaluminum, dialkylaluminum hydrides are formed in situ , and these compounds underwent hydroalumination instead of carboalumination (Scheme 34a ). 18 87 Carboalumination also does not occur with terminal alkynes, which instead undergo metalation at the terminal C–H bond (Scheme 34b ). 88…”

Section: Uncatalyzed Carboalumination Of Alkynesmentioning

confidence: 99%

“…The present short review builds upon the last detailed review, which appeared forty years ago. 17,18 2 Uncatalyzed Carboboration of Alkenes…”

Section: Introductionmentioning

confidence: 99%

Uncatalyzed Carbometallation Involving Group 13 Elements: Carboboration and Carboalumination of Alkenes and Alkynes

Woerpel¹,

Liu²

2022

Synthesis

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Carbometallations of alkenes and alkynes are powerful carbon–carbon bond-forming reactions. The use of compounds containing bonds between carbon and group 13 elements, particularly boron and aluminum, are particularly attractive because of the versatility of subsequent transformations. Uncatalyzed carboboration and carboalumination represent less common classes of reactions. This Short Review discusses uncatalyzed carboboration and carboalumination reactions of alkenes and alkynes, including the reaction design and mechanisms.1 Introduction2 Uncatalyzed Carboboration of Alkenes3 Uncatalyzed Carboboration of Alkynes4 Uncatalyzed Carboalumination of Alkenes5 Uncatalyzed Carboalumination of Alkynes6 Conclusion

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Diisobutylaluminum Hydride

Galatsis¹

2001

Encyclopedia of Reagents for Organic Synthesis

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Compounds of Aluminum in Organic Synthesis

Cited by 21 publications

References 343 publications

Carboalumination of Seven-Membered-Ring trans-Alkenes

Carboalumination of Seven-Membered-Ring trans-Alkenes

Uncatalyzed Carbometallation Involving Group 13 Elements: Carboboration and Carboalumination of Alkenes and Alkynes

Diisobutylaluminum Hydride

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