Iron-catalyzed allylic substitution reactions of allylic ethers with Grignard reagents

Qi, Longying; Ma, Enlu; Fan, Jin; Li, Zhiping

doi:10.1016/j.tetlet.2016.04.027

Cited by 29 publications

(16 citation statements)

References 65 publications

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“…Ar elated iron-catalyzed cross-couplingo fa ctivated aryl allyl ethers with aryl and alkyl Grignard reagents was reported by Li and co-workers(not shown). [53]…”

Section: Cross-coupling Of Ethers and Alcoholsmentioning

confidence: 99%

Iron‐Catalyzed C−O Bond Activation: Opportunity for Sustainable Catalysis

2017

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Oxygen-based electrophiles have emerged as some of the most valuable cross-coupling partners in organic synthesis due to several major strategic and environmental benefits, such as abundance and potential to avoid toxic halide waste. In this context, iron-catalyzed C-O activation/cross-coupling holds particular promise to achieve sustainable catalytic protocols due to its natural abundance, inherent low toxicity, and excellent economic and ecological profile. Recently, tremendous progress has been achieved in the development of new methods for functional-group-tolerant iron-catalyzed cross-coupling reactions by selective C-O cleavage. These methods establish highly attractive alternatives to traditional cross-coupling reactions by using halides as electrophilic partners. In particular, new easily accessible oxygen-based electrophiles have emerged as substrates in iron-catalyzed cross-coupling reactions, which significantly broaden the scope of this catalysis platform. New mechanistic manifolds involving iron catalysis have been established; thus opening up vistas for the development of a wide range of unprecedented reactions. The synthetic potential of this sustainable mode of reactivity has been highlighted by the development of new strategies in the construction of complex motifs, including in target synthesis. The most recent advances in sustainable iron-catalyzed cross-coupling of C-O-based electrophiles are reviewed, with a focus on both mechanistic aspects and synthetic utility. It should be noted that this catalytic manifold provides access to motifs that are often not easily available by other methods, such as the assembly of stereodefined dienes or C(sp )-C(sp ) cross-couplings, thus emphasizing the synthetic importance of this mode of reactivity.

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“…Ar elated iron-catalyzed cross-couplingo fa ctivated aryl allyl ethers with aryl and alkyl Grignard reagents was reported by Li and co-workers(not shown). [53]…”

Section: Cross-coupling Of Ethers and Alcoholsmentioning

confidence: 99%

Iron‐Catalyzed C−O Bond Activation: Opportunity for Sustainable Catalysis

2017

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“…[23][24][25][26] Arylations of selected allyl alcohol derivatives with aryl-Grignard reagents have been reported by Li and coworkers and us. 15,27 We envisioned the development of an Fe-catalysed cross-coupling between alkylmagnesium reagents and diverse allyl acetates that benets from the intrinsic properties of allyl acetates as activated C-electrophiles and the utility of the pendant alkene moiety for further manipulation. While being a formal sp 3electrophile, allyl-X substrates exhibit strikingly different reactivity patterns than alkyl-electrophiles due to the vicinal alkenyl moiety, the absence of b-hydrogen atoms, and the ability to engage in h 3 -coordination to transition metals.…”

Section: Introductionmentioning

confidence: 99%

Iron-catalysed allylation–hydrogenation sequences as masked alkyl–alkyl cross-couplings

Bernauer

Wangelin

2019

RSC Adv.

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“…Mostly, enantioselective allylation reactions have been investigated. For regioselective allylation, a number of transition metal catalysts, such as Cu (27)(28)(29)(30), Ni (31,32), Pd (33,34), Co (35,36) and Fe (37) have been used. However, much research has been directed to the use of different ligands for catalysts to see their effect on the outcome of the reaction.…”

Section: Methodsmentioning

confidence: 99%

Allylation of Aryl Grignard Reagents in the Presence of Transition Metal Catalysis and Organic Catalysis

Kalkan¹

2017

Journal of the Turkish Chemical Society, Section A: Chemistry

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The allylation yield and regioselectivity of phenyl Grignard reagent in THF was investigated in the presence of complexed transition metals and also uncomplexed or complexed transition metal salts. Additionally, the effect of Lewis acids and Lewis bases on the yield and the regioselectivity of the allylic arylation was also observed. Neither P-containing ligands for transition metal complexes, nor transition metal salts did make a difference on the yield and : product ratio and gave the is -product as the main product. However, donor cosolvents resulted in decrease in the yield and change of the regioselectivity.

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Iron-catalyzed allylic substitution reactions of allylic ethers with Grignard reagents

Cited by 29 publications

References 65 publications

Iron‐Catalyzed C−O Bond Activation: Opportunity for Sustainable Catalysis

Iron‐Catalyzed C−O Bond Activation: Opportunity for Sustainable Catalysis

Iron-catalysed allylation–hydrogenation sequences as masked alkyl–alkyl cross-couplings

Allylation of Aryl Grignard Reagents in the Presence of Transition Metal Catalysis and Organic Catalysis

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