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Literature DB >> 17655319

Iron-catalyzed alkylation of alkenyl Grignard reagents.

Gérard Cahiez¹, Christophe Duplais, Alban Moyeux.

Abstract

The first iron-catalyzed cross-coupling reaction between alkenyl Grignard reagents and n- or s-alkyl bromides is described. The reaction is stereoselective and takes place in the presence of 5 mol % of [Fe(acac)3/TMEDA/HMTA] (1:2:1) under very mild conditions (THF, 0 degrees C, 45 min).

Entities: Chemical

Year: 2007 PMID： 17655319 DOI： 10.1021/ol7016092

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

13 in total

1. A Physical-Inorganic Approach for the Elucidation of Active Iron Species and Mechanism in Iron-Catalyzed Cross-Coupling.

Authors: Stephanie H Carpenter; Michael L Neidig
Journal: Isr J Chem Date: 2017-08-24 Impact factor: 3.333

2. Intermediates and Reactivity in Iron-Catalyzed Cross-Couplings of Alkynyl Grignards with Alkyl Halides.

Authors: Jared L Kneebone; William W Brennessel; Michael L Neidig
Journal: J Am Chem Soc Date: 2017-05-16 Impact factor: 15.419

3. Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer.

Authors: Michael T Bovino; Sherry R Chemler
Journal: Angew Chem Int Ed Engl Date: 2012-03-05 Impact factor: 15.336

4. Iron-catalyzed cross-coupling of unactivated secondary alkyl thio ethers and sulfones with aryl Grignard reagents.

Authors: Scott E Denmark; Alexander J Cresswell
Journal: J Org Chem Date: 2013-11-20 Impact factor: 4.354

5. Additive and Counterion Effects in Iron-Catalyzed Reactions Relevant to C-C Bond Formation.

Authors: Nikki J Bakas; Michael L Neidig
Journal: ACS Catal Date: 2021-06-29 Impact factor: 13.700

6. Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and Aryl Bromides in Water at Room Temperature.

Authors: Christophe Duplais; Arkady Krasovskiy; Bruce H Lipshutz
Journal: Organometallics Date: 2011-11-21 Impact factor: 3.876

Iron-catalyzed alkylation of alkenyl Grignard reagents.

1. A Physical-Inorganic Approach for the Elucidation of Active Iron Species and Mechanism in Iron-Catalyzed Cross-Coupling.

2. Intermediates and Reactivity in Iron-Catalyzed Cross-Couplings of Alkynyl Grignards with Alkyl Halides.

3. Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer.

4. Iron-catalyzed cross-coupling of unactivated secondary alkyl thio ethers and sulfones with aryl Grignard reagents.

5. Additive and Counterion Effects in Iron-Catalyzed Reactions Relevant to C-C Bond Formation.

6. Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and Aryl Bromides in Water at Room Temperature.

7. Development and Evolution of Mechanistic Understanding in Iron-Catalyzed Cross-Coupling.

8. Intermediates and Mechanism in Iron-Catalyzed Cross-Coupling.

9. A TMEDA-Iron Adduct Reaction Manifold in Iron-Catalyzed C(sp² )-C(sp³ ) Cross-Coupling Reactions.

10. Stereospecific Ni-catalyzed cross-coupling of potassium alkenyltrifluoroborates with alkyl halides.