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Literature DB >> 11397172

Selective halogen-magnesium exchange reaction via organomagnesium ate complex.

A Inoue¹, K Kitagawa, H Shinokubo, K Oshima.

Abstract

Halogen-magnesium exchange of various aryl halides is achieved with a magnesium ate complex at low temperatures. Tributylmagnesate (nBu3MgLi) induces facile iodine-magnesium exchange at -78 degrees C. Dibutylisopropylmagnesate (iPr(n)Bu2MgLi) is more reactive than nBu3MgLi, and this reagent accomplishes selective bromine-magnesium exchange at -78 degrees C. This procedure is utilized for the preparation of various polyfunctionalized arylmagnesium species. The exchange of alkenyl halides using this method proceeds with retention of configuration of the double bond.

Entities: Chemical

Year: 2001 PMID： 11397172 DOI： 10.1021/jo015597v

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

13 in total

1. Magnesiate Addition/Ring-Expansion Strategy To Access the 6-7-6 Tricyclic Core of Hetisine-Type C₂₀-Diterpenoid Alkaloids.

Authors: Jason J Pflueger; Louis C Morrill; Justine N deGruyter; Melecio A Perea; Richmond Sarpong
Journal: Org Lett Date: 2017-08-18 Impact factor: 6.005

2. Linchpin synthons: metalation of aryl bromides bearing a potassium trifluoroborate moiety.

Authors: Gary A Molander; Noel M Ellis
Journal: J Org Chem Date: 2006-09-15 Impact factor: 4.354

3. Cyclic oxonitriles: stereodivergent grignard addition-alkylations.

Authors: Fraser F Fleming; Guoqing Wei; Zhiyu Zhang; Omar W Steward
Journal: J Org Chem Date: 2007-06-13 Impact factor: 4.354

4. A multifaceted phosphate tether: application to the C15-C30 subunit of dolabelides A-D.

Authors: Alan Whitehead; Joshua D Waetzig; Christopher D Thomas; Paul R Hanson
Journal: Org Lett Date: 2008-03-07 Impact factor: 6.005

5. Main group multiple C-H/N-H bond activation of a diamine and isolation of a molecular dilithium zincate hydride: experimental and DFT evidence for alkali metal-zinc synergistic effects.

Authors: Ross Campbell; Daniel Cannon; Pablo García-Álvarez; Alan R Kennedy; Robert E Mulvey; Stuart D Robertson; Jörg Sassmannshausen; Tell Tuttle
Journal: J Am Chem Soc Date: 2011-08-04 Impact factor: 15.419

6. A mild synthesis of new aryl vinyl ethers and diethyl 1-[(alkyl)(cyano)methyl]vinylphosphonates via the substitution of a 2,3-difunctional allyl bromide.

Authors: Asma Fray; Jihène Ben Kraïem; Aïcha Arfaoui; Hassen Amri
Journal: ScientificWorldJournal Date: 2014-02-12

Selective halogen-magnesium exchange reaction via organomagnesium ate complex.

1. Magnesiate Addition/Ring-Expansion Strategy To Access the 6-7-6 Tricyclic Core of Hetisine-Type C₂₀-Diterpenoid Alkaloids.

2. Linchpin synthons: metalation of aryl bromides bearing a potassium trifluoroborate moiety.

3. Cyclic oxonitriles: stereodivergent grignard addition-alkylations.

4. A multifaceted phosphate tether: application to the C15-C30 subunit of dolabelides A-D.

5. Main group multiple C-H/N-H bond activation of a diamine and isolation of a molecular dilithium zincate hydride: experimental and DFT evidence for alkali metal-zinc synergistic effects.

6. A mild synthesis of new aryl vinyl ethers and diethyl 1-[(alkyl)(cyano)methyl]vinylphosphonates via the substitution of a 2,3-difunctional allyl bromide.

7. Synthesis of 3,3'-di-O-methyl ardimerin and exploration of its DNA binding properties.

8. Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation.

9. Synthesis of the benzo-fused indolizidine alkaloid mimics.

10. Stereoretentive Pd-catalyzed Kumada-Corriu couplings of alkenyl halides at room temperature.