Nucleophilic Addition to Electron-deficient CC Double Bonds

2005 ◽  
pp. 45-84 ◽  
Keyword(s):  
Nucleophilic Addition ◽  
Double Bonds

Mechanisms of nucleophilic addition to activated double bonds: 1,2- and 1,4-Michael addition of ammonia

1993 ◽  
Vol 115 (18) ◽  
pp. 8263-8269 ◽  
Author(s):  
Leonardo Pardo ◽  
Roman Osman ◽  
Harel Weinstein ◽  
James R. Rabinowitz
Keyword(s):  
Michael Addition ◽  
Nucleophilic Addition ◽  
Double Bonds

Reactions of bridging C3 ligands in diiron complexes: Unconventional routes to new functionalized organic frames

2010 ◽  
Vol 82 (7) ◽  
pp. 1555-1568 ◽  
Author(s):  
Valerio Zanotti
Keyword(s):  
Functional Groups ◽  
Nucleophilic Addition ◽  
Metal Center ◽  
Unusual Reaction ◽  
Nucleophilic Attack ◽  
Double Bonds ◽  
Bridging Ligands ◽  
Reaction Patterns

Diiron complexes containing C3 ligands, such as vinyliminium and vinylalkylidene bridging units, display unusual reaction patterns, not observed when the same organic fragments are bound to a single metal center, or not coordinated. Bridging vinyliminium complexes [Fe2{μ-η1:η3-C(NMe2)CH=CR}(μ-CO)(CO)(Cp)2][SO3CF3] undergo nucleophilic addition at the iminium C or at α-C position, which is uncommon since non-coordinated vinyliminium species generally undergo conjugated (Michael type) nucleophilic attack. Likewise, bridging vinyliminium ligands undergo new and unusual transformations consisting of the deprotonation and replacement of the α-CH by a variety of functional groups. These reactions, resulting in the formation of C–C and C–heteroatom single and double bonds, produce new bridging ligands of the type [μ-C(NMe2)C(X)CR) (X = S, O, Se, SPh, CNMe, NNCHCO2Me]. Removal of the vinylalkylidene ligands from the bridging coordination is achieved by a [3 + 2] cycloaddition with alkynes. The reaction leads to the formation of ferrocenes containing one polysubstituted Cp ring, which results from the cycloaddition of the bridging C3 ligand with alkynes. This result suggests a new possible route for the synthesis of polyfunctionalized ferrocenes.

scholarly journals A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids

2014 ◽  
Vol 10 ◽  
pp. 722-731
Author(s):  
Natalia V Pavlenko ◽  
Tatiana I Oos ◽  
Yurii L Yagupolskii ◽  
Igor I Gerus ◽  
Uwe Doeller ◽  
...  
Keyword(s):  
Amino Acids ◽  
Ethyl Ester ◽  
Nucleophilic Addition ◽  
Phosphinic Acid ◽  
Double Bonds ◽  
Synthetic Methodology ◽  
One Pot ◽  
Phosphinic Acids

A series of novel (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of proteinogenic and nonproteinogenic α-amino acids were prepared. The synthetic methodology was based on nucleophilic addition of (trifluoromethyl)phosphinic acid or (difluoromethyl)phosphinic acid or its ethyl ester to substrates with C=N or activated C=C double bonds. Analogues of glycine, phenylglycine, alanine, valine, proline, aminomalonic and aspartic acids were thus prepared. Three-component one-pot reactions of (trifluoromethyl)phosphinic acid and dibenzylamine with aldehydes were also tested to prepare the title compounds.

Transition metal-catalyzed direct nucleophilic addition of C–H bonds to carbon–heteroatom double bonds

2014 ◽  
Vol 5 (6) ◽  
pp. 2146-2159 ◽  
Author(s):  
Xi-Sha Zhang ◽  
Kang Chen ◽  
Zhang-Jie Shi
Keyword(s):  
Transition Metal ◽  
Nucleophilic Addition ◽  
Transition Metal Catalysis ◽  
Grignard Reaction ◽  
Double Bonds ◽  
Metal Catalysis ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Compared with the traditional Grignard reaction, direct insertion of polar double bonds to C–H bonds via transition-metal catalysis is ideal from the viewpoint of atom-, step- and cost-economy and the avoidance of the waste emission, as well as of the complex manipulation of sensitive reagents.

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