Iron catalyzed cross-coupling reactions. Synthesis of arylethenes.

Molander, Gary A.; RAHN, B. J.; Shubert, David C.; Bonde, Steven E.

doi:10.1016/s0040-4039(00)94109-1

Cited by 117 publications

(31 citation statements)

References 21 publications

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“…[65] The use of Fe(acac) 3 as a source of Fe III has been investigated by numerous groups because of its superior ease of handling compared to highly hygroscopic FeCl 3 . [39,50,51,55,60,66,67] Generally, it was found that using additives such as TMEDA, NMP, or hexamethylenetetramine (HMTA) with Fe(acac) 3 improved selectivity for cross-coupling over homo-coupling of the Grignard reagent. Recently, we reported on Fe III compounds supported by tetradentate and tridentate (amine)bis(phenolato) ligands, which are effective catalysts for cross-coupling of aryl Grignard reagents with alkyl halides, including secondary alkyl halides and benzyl halides.…”

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confidence: 99%

Synthesis, Structure, and C–C Cross‐Coupling Activity of (Amine)bis(phenolato)iron(acac) Complexes

2011

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A series of (amine)bis(phenolato)iron(III)acac complexes has been prepared and characterized. Reaction of Fe(acac)3 with the diprotonated linear tetradentate proligand N,N′‐bis(4,6‐di‐tert‐butyl‐2‐methylphenol)‐N,N′‐dimethyl‐1,2‐diaminoethane, H2[L1], and tripodal tetradentate ligand precursors dimethylaminoethylamino‐N,N‐bis(2‐methylene‐4,6‐di‐tert‐butylphenol), H2[L2], dimethylaminoethylamino‐N,N‐bis(2‐methylene‐4‐methyl‐6‐tert‐butylphenol), H2[L3], 2‐methoxyethylamino‐N,N‐bis(2‐methylene‐4,6‐di‐tert‐butylphenol), H2[L4], 2‐methoxyethylamino‐N,N‐bis(2‐methylene‐4‐methyl‐6‐tert‐butylphenol), H2[L5], and 2‐methoxyethylamino‐N,N‐bis(2‐methylene‐4,6‐dimethylphenol), H2[L6], produces the distorted octahedral FeIII complexes [L1]Fe(acac) (1), [L2]Fe(acac) (2), [L3]Fe(acac) (3), [L4]Fe(acac) (4), [L5]Fe(acac) (5), and [L6]Fe(acac) (6). In all of these complexes, the phenolato oxygen atoms are cis‐oriented. The paramagnetic FeIII complexes 1–6 were also characterized by UV/Vis and IR spectroscopy, mass spectrometry, cyclic voltammetry, and magnetic measurements. Single crystal X‐ray molecular structures have been determined for complexes 1, 2, 3, 5, and the proligand H2[L6]. Preliminary investigations of complexes 1–6 for catalytic cross‐coupling reactions of aryl Grignard reagents with cyclic and acyclic secondary alkyl halides and benzyl halides were performed. While the activity for cyclohexyl chlorides and bromides was high, cross‐coupling of benzyl halides was moderate and 2‐bromo‐ and 2‐chlorobutane gave poor yields of cross‐coupled product.

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confidence: 99%

Synthesis, Structure, and C–C Cross‐Coupling Activity of (Amine)bis(phenolato)iron(acac) Complexes

2011

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“…In the meantime, iron catalysts have become very popular for related reactions. [15][16][17][18][19][20][21][22][23][24][25] Recently, Sonogashira-Hagihara, [26,27] Mizoroki-Heck [28] and Suzuki-Miyaura C-C cross-coupling reactions [29] have been catalyzed by iron salts or iron complexes.…”

Section: Resultsmentioning

confidence: 99%

Ligandless Iron‐Catalyzed Desulfinylative C–C Allylation Reactions using Grignard Reagents and Alk‐2‐enesulfonyl Chlorides

et al. 2009

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Alk-2-enesulfonyl chlorides 1-4 were synthesized by the BCl 3 -promoted ene reaction of alkenes with SO 2 . These sulfonyl chlorides were then used as electrophilic partners in iron-catalyzed desulfinylative cross-coupling reactions with different Grignard reagents (aromatic, aliphatic, and heteroaromatic). The reaction can be catalyzed with even 2 mol-% of the simple iron salt Fe(acac) 3 . The regioselectivity of these allylations was studied by using sulfonyl chlorides 3

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“…[8,9] However, in 1982 Julia and co-workers [10] reported the Fe-catalyzed CÀC crosscoupling reaction of Grignard reagents with vinylic sulfones, while in 1983 Molander et al reported the Fe-catalyzed crosscoupling of aryl Grignard reagents with alkenyl halides, [11] and in 1984 Marchese and co-workers [12] developed the Fe-catalyzed acylation of Grignard reagents [Scheme 1, Equation (2)].…”

Section: Dedicated To Professor Horst Prinzbach On the Occasion Of Himentioning

confidence: 99%

Iron‐Catalyzed Desulfinylative CC Cross‐Coupling Reactions of Sulfonyl Chlorides with Grignard Reagents

Volla

Vogel

2008

Angewandte Chemie

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Iron catalyzed cross-coupling reactions. Synthesis of arylethenes.

Cited by 117 publications

References 21 publications

Synthesis, Structure, and C–C Cross‐Coupling Activity of (Amine)bis(phenolato)iron(acac) Complexes

Synthesis, Structure, and C–C Cross‐Coupling Activity of (Amine)bis(phenolato)iron(acac) Complexes

Ligandless Iron‐Catalyzed Desulfinylative C–C Allylation Reactions using Grignard Reagents and Alk‐2‐enesulfonyl Chlorides

Iron‐Catalyzed Desulfinylative CC Cross‐Coupling Reactions of Sulfonyl Chlorides with Grignard Reagents

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