Iron‐Catalyzed Borrowing Hydrogen <i>C</i>‐Alkylation of Oxindoles with Alcohols

Dambatta, Mubarak B.; Polidano, Kurt; Northey, Alexander D.; Williams, Jonathan M. J.; Morrill, Louis C.

doi:10.1002/cssc.201900799

Cited by 59 publications

(43 citation statements)

References 102 publications

(14 reference statements)

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“…HB methylation of 2‐oxindoles and indoles reported by Morrill (A), indole alkylation reported by Renaud and co‐workers (B), and alkylation of 2‐oxindole reported by Morrill (C) …”

Section: Applications In Reactions Involving Ht Stepsmentioning

confidence: 91%

“…A more thorough study on indole alkylation was simultaneously reported by Renaud and co‐workers using pre‐catalysts 1f and 5fa (Scheme B): a series of benzylic as well as aliphatic alcohols were employed as alkylating agents. Very recently, Morrill and co‐workers extended the scope of oxindole alkylation to several different 2‐oxindoles and to a number of benzylic and aliphatic alcohols (Scheme C) …”

Section: Applications In Reactions Involving Ht Stepsmentioning

confidence: 99%

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Recent Catalytic Applications of (Cyclopentadienone)iron Complexes

Pignataro

Gennari

2020

Eur J Org Chem

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(Cyclopentadienone)iron complexes (CICs) are attractive pre‐catalysts due to their easy preparation and robustness, which are uncommon features in homogeneous iron catalysis. They represent a striking example of how deeply a non‐innocent ligand may affect the catalytic properties of the metal. Swinging between the cyclopentadienone and the hydroxycyclopentadienyl form, the ligand induces iron to engage in H2 heterolytic cleavage and transfer. The latter represents the basis for numerous applications of CICs in redox chemistry (multiple bond reduction, alcohol oxidation) and “hydrogen borrowing” processes (e.g., alcohol amination) that have been reported over the last few years. Moreover, very recently catalytic applications of CICs in different types of reactivity (where again the non‐innocent ligand plays a key role), have appeared in the literature. This minireview summarizes the advancements that have been made in the field of CICs and their catalytic applications in the period 2014–2019.

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“…HB methylation of 2‐oxindoles and indoles reported by Morrill (A), indole alkylation reported by Renaud and co‐workers (B), and alkylation of 2‐oxindole reported by Morrill (C) …”

Section: Applications In Reactions Involving Ht Stepsmentioning

confidence: 91%

Section: Applications In Reactions Involving Ht Stepsmentioning

confidence: 99%

Recent Catalytic Applications of (Cyclopentadienone)iron Complexes

Pignataro

Gennari

2020

Eur J Org Chem

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“…I-V (Moulin et al, 2013) and cat. VI (Dambatta et al, 2019) were prepared according to the literature. All commercially available reagents and solvents (purchased from Sigma-Aldrich, TCI, Alfa-Aesar and Acros) were used without further purification unless otherwise noted.…”

Section: Methodsmentioning

confidence: 99%

Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles

et al. 2020

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Benzimidazoles are important N-heteroaromatic compounds with various biological activities and pharmacological applications. Herein, we present the first iron-catalyzed selective synthesis of 1,2-disubstituted benzimidazoles via acceptorless dehydrogenative coupling of primary alcohols with aromatic diamines. The tricarbonyl (η 4-cyclopentadienone) iron complex catalyzed dehydrogenative cyclization, releasing water and hydrogen gas as by-products. The earth abundance and low toxicity of iron metal enable the provision of an eco-friendly and efficient catalytic method for the synthesis of benzimidazoles.

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“…In 2015, we introduced in catalysis the tricarbonyl iron complex Fe2 bearing a diaminocyclopentadienone ligand [21]. Compared to other cyclopentadienone iron carbonyl complexes, this phosphine-free iron complex has, to the best of our knowledge, the highest catalytic activities to date in reductive amination [21], in chemoselective reduction of α,β-unsaturated ketones [22], in the hydrogenation of carbon dioxide [23], in alkylation of ketones [24][25][26][27], amines [25,28], oxindoles [29], indoles [25,30] and alcohols [31,32]. In our ongoing interest in reduction and alkylation, we thought that a water-soluble analog of Fe2 would be more active than our previous water-soluble cyclopentadienone iron complex Fe3 (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Cyclopentadienone Iron Tricarbonyl Complexes-Catalyzed Hydrogen Transfer in Water

et al. 2020

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The development of efficient and low-cost catalytic systems is important for the replacement of robust noble metal complexes. The synthesis and application of a stable, phosphine-free, water-soluble cyclopentadienone iron tricarbonyl complex in the reduction of polarized double bonds in pure water is reported. In the presence of cationic bifunctional iron complexes, a variety of alcohols and amines were prepared in good yields under mild reaction conditions.

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Iron‐Catalyzed Borrowing Hydrogen C‐Alkylation of Oxindoles with Alcohols

Cited by 59 publications

References 102 publications

Recent Catalytic Applications of (Cyclopentadienone)iron Complexes

Recent Catalytic Applications of (Cyclopentadienone)iron Complexes

Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles

Cyclopentadienone Iron Tricarbonyl Complexes-Catalyzed Hydrogen Transfer in Water

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