Reactions of Alkyllithium and Grignard Reagents with (Cyclopentadienyl)dicarbonyl(2-methylbutadiene)molybdenum: Observations of Solvent Effects on Regioselectivity

1994 ◽  
Vol 13 (7) ◽  
pp. 2539-2541 ◽  
Author(s):  
Anthony J. Pearson ◽  
M. K. Manoj Babu
Keyword(s):  
Solvent Effects ◽  
Grignard Reagents

Reactions of Norbornen-7-one with Organolithium Reagents

1971 ◽  
Vol 49 (13) ◽  
pp. 2223-2228 ◽  
Author(s):  
F. R. S. Clark ◽  
J. Warkentin
Keyword(s):  
Solvent Effects ◽  
Grignard Reagents ◽  
Organolithium Reagents

Alkyllithium reagents (RLi: R = methyl, n-butyl, t-butyl) add to norbornen-7-one either without stereochemical preference (R = n-butyl) or with syn attack favored. This addition selectivity is qualitatively the same as that shown by corresponding alkylmagnesium reagents but competition from reduction is much less important in the case of alkyllithium reagents.Phenyllithium and vinyllithium add preferentially from the anti face, although the corresponding Grignard reagents add selectively from the syn face. Possible causes of the stereoselectivities are considered. Solvent effects on the stereochemistry of addition are small.

Control of Diastereoselectivity by Solvent Effects in the Addition of Grignard Reagents to Enantiopuret-Butylsulfinimine:  Syntheses of the Stereoisomers of the Hydroxyl Derivatives of Sibutramine

2005 ◽  
Vol 7 (13) ◽  
pp. 2599-2602 ◽  
Author(s):  
Bruce Z. Lu ◽  
Chris Senanayake ◽  
Nansheng Li ◽  
Zhengxu Han ◽  
Roger P. Bakale ◽  
...  
Keyword(s):  
Solvent Effects ◽  
Grignard Reagents ◽  
Derivatives Of

Fe-Catalyzed Conjunctive Cross-Couplings of Unactivated Alkenes with Grignard Reagents

2020 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Cassandra R. Youshaw ◽  
Mingbin Yuan ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Functional Groups ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Turnover Frequency ◽  
Diverse Range ◽  
Cascade Cyclization ◽  
Radical Cascade

The first iron-catalyzed three-component cross-coupling of unactivated olefins with alkyl halides and Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp2-hybridized nucleophiles, alkyl halides, and unactivated olefins bearing diverse functional groups to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C-C bonds.

Kinetic Solvent Effects in Organic Reactions

2017 ◽  
Author(s):  
Belinda Slakman ◽  
Richard West
Keyword(s):  
Solvent Effect ◽  
Reaction Kinetics ◽  
Computational Methods ◽  
High Throughput ◽  
Kinetic Modeling ◽  
Solvent Effects ◽  
Reaction Rates ◽  
Prior Work ◽  
Solvent Phase ◽  
High Throughput Manner

<div> <div> <div> <p>This article reviews prior work studying reaction kinetics in solution, with the goal of using this information to improve detailed kinetic modeling in the solvent phase. Both experimental and computational methods for calculating reaction rates in liquids are reviewed. Previous studies, which used such methods to determine solvent effects, are then analyzed based on reaction family. Many of these studies correlate kinetic solvent effect with one or more solvent parameters or properties of reacting species, but it is not always possible, and investigations are usually done on too few reactions and solvents to truly generalize. From these studies, we present suggestions on how best to use data to generalize solvent effects for many different reaction types in a high throughput manner. </p> </div> </div> </div>

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