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Synthesis and Reactions of N-Heterocyclic Carbene …

Curran, Disulfides and Boryl Sulfides Serve as Both Initiators and Precatalysts in Radical Reductions of Halides by an N-Heterocyclic Carbene-Borane, Synth.

Curran, Neutral Sulfur Nucleophiles: Synthesis of Thioethers and Thioesters by Substitution Reactions of N-Heterocyclic Carbene Boryl Sulfides and Thioamides, Org.

Curran, [3 + 2]-Dipolar Cycloaddition Reactions of an N-Heterocyclic Carbene Boryl Azide, Org.

Synthesis and Reactions of N-Heterocyclic ..

Curran, Reactions of Boron-Substituted N-Heterocyclic Carbene Boranes with Triflic Acid.

(2015)Synthesis and Reactions of Heterosubstituted N-Heterocyclic Carbene-Boranes. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

Curran, Radical Reactions of N-Heterocyclic Carbene Boranes with Organic Nitriles: Cyanation of NHC-Boranes and Reductive Decyanation of Malononitriles, J.

Synthesis and Reactions of N‐Heterocyclic Carbene …

Carbene-boranes 1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene borane (dipp-Imd-BH3) and 1,3-dimethylimidazol-2-ylidene borane (diMe-Imd-BH3) were treated with various electrophiles to compare reactivity of carbene-borane with nucleophilicity values of carbene-borane (dipp-Imd-BH3 = 9.55 N, diMe-Imd-BH3 = 11.88 N). Compounds with electrophilicity values greater –15 E reacted rapidly with carbene-borane, but compounds with electrophilicity values less than –15 E reacted slowly or not at all with carbene-borane. Hydroboration complexes were isolated from the reactions of diMe-Imd-BH3 with benzylidenemalononitrile and 2-ethylidenemalononitrile. Overall the reactivity of carbene-borane matched predictions based on nucleophilicity and electrophilicity values.
Carbene-boranes were also treated with acid halides and halogens to form halogenated carbene-boranes. Iodination occurs most rapidly followed by bromination and then chlorination. Dipp-Imd-BH3 can only be iodinated once likely due to the steric bulk around the boron atom while diMe-Imd-BH3 can be iodinated once (0.5 equiv of I2 added) or twice (1.0 equiv of I2 added). Tribromination and trichlorination was possible for both carbene-boranes. Disproportionation of the halides bonded to the boron atoms occurred rapidly with iodide and slowly with bromide. These halogenated carbene-boranes also were reduced by lithium aluminum deuteride to give selectively deuterated carbene-borane species, and also underwent nucleophilic substitutions to give carbene-boryl-azide.
[3+2]-Dipolar cycloaddition reactions were performed on carbene-boryl-azide with electron deficient alkynes, alkenes, and nitriles to give new carbene-boryl-triazoles, -triazolidines, and -tetrazoles. Electron deficient alkynes and alkenes such as propiolate and acrylate were reactive with carbene-boryl-azide even at room temperature, but less electron deficient alkynes, nitriles, and alkenes required heating or microwave radiation to form cycloaddition borane products.
Carbene-boryl-triazoles are very robust and can withstand reductive and acidic conditions. The triazole can even be methylated by methyl iodide or methyl triflate to give a carbene-boryl-triazole salt. The triazole could be detached from the boron atom by reacting the boron atom with halogen, and decomplexing the carbene-borane in methanol.

P.. "Complexes of borane and N-heterocyclic carbenes: A new class of radical hydrogen atom donor,"

Lacôte, Electron Paramagnetic Resonance and Computational Studies of Radicals Derived from Boron-Substituted N-Heterocyclic Carbene Boranes, J.

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Synthesis and Reactions of N‐Heterocyclic Carbene ..


The synthesis of chiral N-heterocyclic carbene–borane …

Curran, Tetrahydrofuran Ring Opening and Related Reactions with an N-Heterocyclic Carbene-Boryl Trifluoromethanesulfonate, Dalton Trans., 2012, 42, 695-700.

Synthesis and Reactions of N-Heterocyclic Carbene ..

Lacôte, Mechanistic and Preparative Studies of Radical Chain Homolytic Substitution Reactions of N-Heterocyclic Carbene Boranes and Disulfides, J.

Boron-hydrogen bond insertion reactions of N-heterocyclic carbene ..

: Structure of thiaminepyrophosphate (xvi); : a disilicon(0) species (xvii) stabilized by ‐heterocyclic carbene ligands; : cleavage product (xviii) of xvii upon treatment with diborane, resulting in a hitherto unprecedented silylene/carbene species.

2011) Synthesis and reactions of N-heterocyclic ..

11449-114.

Solovyev, Andrey; Chu, Qianli; Geib, Steven J.; Fensterbank, Louis; Malacria, Max; Lacôte, Emmanuel; Curran, Dennis P.; . "Substitution Reactions at Tetracoordinate Boron: Synthesis of N-Heterocyclic Carbene Boranes with Boron-Heteroatom Bonds,"

Curran, Synthesis and Suzuki Reactions of N-Heterocyclic ..

Carbene-boranes 1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene borane (dipp-Imd-BH3) and 1,3-dimethylimidazol-2-ylidene borane (diMe-Imd-BH3) were treated with various electrophiles to compare reactivity of carbene-borane with nucleophilicity values of carbene-borane (dipp-Imd-BH3 = 9.55 N, diMe-Imd-BH3 = 11.88 N). Compounds with electrophilicity values greater –15 E reacted rapidly with carbene-borane, but compounds with electrophilicity values less than –15 E reacted slowly or not at all with carbene-borane. Hydroboration complexes were isolated from the reactions of diMe-Imd-BH3 with benzylidenemalononitrile and 2-ethylidenemalononitrile. Overall the reactivity of carbene-borane matched predictions based on nucleophilicity and electrophilicity values.
Carbene-boranes were also treated with acid halides and halogens to form halogenated carbene-boranes. Iodination occurs most rapidly followed by bromination and then chlorination. Dipp-Imd-BH3 can only be iodinated once likely due to the steric bulk around the boron atom while diMe-Imd-BH3 can be iodinated once (0.5 equiv of I2 added) or twice (1.0 equiv of I2 added). Tribromination and trichlorination was possible for both carbene-boranes. Disproportionation of the halides bonded to the boron atoms occurred rapidly with iodide and slowly with bromide. These halogenated carbene-boranes also were reduced by lithium aluminum deuteride to give selectively deuterated carbene-borane species, and also underwent nucleophilic substitutions to give carbene-boryl-azide.
[3+2]-Dipolar cycloaddition reactions were performed on carbene-boryl-azide with electron deficient alkynes, alkenes, and nitriles to give new carbene-boryl-triazoles, -triazolidines, and -tetrazoles. Electron deficient alkynes and alkenes such as propiolate and acrylate were reactive with carbene-boryl-azide even at room temperature, but less electron deficient alkynes, nitriles, and alkenes required heating or microwave radiation to form cycloaddition borane products.
Carbene-boryl-triazoles are very robust and can withstand reductive and acidic conditions. The triazole can even be methylated by methyl iodide or methyl triflate to give a carbene-boryl-triazole salt. The triazole could be detached from the boron atom by reacting the boron atom with halogen, and decomplexing the carbene-borane in methanol.

The synthesis of chiral N-heterocyclic carbene–borane and ..

2261-2267.

Ueng, Shau-Hua; Fensterbank, Louis; Lacôte, Emmanuel; Malacria, Max; Curran, Dennis P.; . "Radical Deoxygenation of Xanthates and Related Functional Groups with New Minimalist N-Heterocyclic Carbene Boranes,"

Synthesis and reactions of N-heterocyclic ..

Lalevée, Formation of N-Heterocyclic Carbene-Boryl Radicals through Electrochemical and Photochemical Cleavage of the B-S Bond in N-Heterocyclic Carbene-Boryl Sulfides, J.

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