Unique reactivity of a 1,4-dilithiobutadiene with methyl iodide

Hudrlik, Paul F.; Donghua, Dai; Hudrlik, Anne M.

doi:10.1016/j.tetlet.2006.03.067

Cited by 4 publications

(1 citation statement)

References 19 publications

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“…We also prepared the lithium reagents 17 possessing a methyl group at position 4 (Scheme ). We found the procedure reported recently by Hudrilik was very effective for preparation of this type of monolithium reagent . However, no intramolecular lithiation-cyclization of 18 took place even at elevated reaction temperatures.…”

Section: Resultsmentioning

confidence: 69%

Cycloaddition Reactions of 1-Lithio-1,3-dienes with Aromatic Nitriles Affording Multiply Substituted Pyridines, Pyrroles, and Linear Butadienylimines

Wang

Liu

et al. 2006

J. Org. Chem.

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Fully or partially substituted 1-iodo- or 1-bromo-1,3-dienes could be readily lithiated using t-BuLi or n-BuLi to afford their corresponding 1-lithio-1,3-diene derivatives in quantitative yields. When these in situ generated lithium reagents were treated with organonitriles, depending on the substitution patterns of the butadienyl skeletons, substituted pyridines, pyrroles, and/or linear butadienyl imines were formed in good to excellent yields via N-lithioketimine intermediates. In the cases of 1,2,3,4-tetrasubstituted and 2,3-disubstituted 1-lithio-1,3-dienes, pyridine derivatives or linear butadienyl imines were generally formed depending on the reaction temperatures. When 1,2,3,4-tetrasubstituted 4-halo-1-lithio-1,3-dienes and 1,2-disubstituted 1-lithio-1,3-dienes were treated with organonitriles, pyrrole derivatives or linear butadienyl imines were obtained. Competition between 5-exo and 6-endo cyclization was found to be responsible for the formation of either pyrroles or pyridines. Selective elimination of RLi from the lithiated cyclic N-containing intermediates was observed. The order of elimination was found to be LiCl > Me3SiLi > LiH.

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Section: Resultsmentioning

confidence: 69%

Cycloaddition Reactions of 1-Lithio-1,3-dienes with Aromatic Nitriles Affording Multiply Substituted Pyridines, Pyrroles, and Linear Butadienylimines

Wang

Liu

et al. 2006

J. Org. Chem.

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1,4‐Diiodo‐1,3‐dienes: Versatile Reagents in Organic Synthesis

Ananikov

Hazipov

Beletskaya

2010

Chemistry An Asian Journal

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1,4-Diiodo-1,3-dienes are unique reagents in organic synthesis and have been employed in several well-known and recently developed areas of application. Furthermore, these dienes are easily accessible, starting from the alkynes and iodine, and they have demonstrated high reactivity in cross-coupling reactions, organometallic synthesis, in the preparation of heterocyclic compounds, and several other transformations. The high reactivity of the 1,4-diiodo-1,3-dienes allows for the development of synthetic procedures that use mild conditions (room temperature). The key advantages in assembling complex organic molecules, natural products, and compounds for material science using 1,4-diiodo-1,3-dienes as building blocks include high yields, excellent selectivity, and diverse reactivity in carbon-carbon and carbon-heteroatom bond formation. This Focus Review describes the scope and application of the 1,4-diiodo-1,3-dienes in organic synthesis as well as summarizes the methods for preparation of the dienes.

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