Iron-catalyzed decarboxylative methylation of α,β-unsaturated acids under ligand-free conditions

Rong, Guangwei; Liu, Defu; Lu, Linhua; Yan, Hong; Zheng, Yang; Chen, Jie; Mao, Jincheng

doi:10.1016/j.tet.2014.06.014

Cited by 41 publications

(17 citation statements)

References 33 publications

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“…(Scheme 311). 582 The reaction was performed using 2 equiv of di-tert-butyl peroxide as oxidant and as source of the methyl group. Iron(III) chloride was employed as catalyst with no need for additional ligands.…”

Section: Decarboxylative and Decarbonylativementioning

confidence: 99%

Iron Catalysis in Organic Synthesis

2015

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Section: Decarboxylative and Decarbonylativementioning

confidence: 99%

Iron Catalysis in Organic Synthesis

2015

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“…The application of DTBP in Scheme is summarized here: 1) synthesis of 144 is demonstrated by an iron‐catalyzed decarboxylative methylation of α,β‐unsaturated acids in the absence of ligands; 2) by using Cu(OAc) 2 as the catalyst, N‐methylation of sulfoximines 145 was developed with good functional group tolerance; 3) a facile and straightforward route to the synthesis of 3‐methylcoumarins 146 was achieved through the radical reaction of coumarins with DTBP catalyzed by CuCl; 4) two different methods of amidic N‐methylation of amides 147 and sulfonamides 148 were developed by Li and Cai. Under the conditions, the methylation selectively occurs on the amidic nitrogen .…”

Section: Methylation By Using Conventional Reagentsmentioning

confidence: 99%

Recent Advances in Methylation: A Guide for Selecting Methylation Reagents

Chen

2018

Chemistry A European J

190

121

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Methylation is a well‐known structural modification in organic and medicinal chemistry. This review summarizes recent advances in methylation by categorizing specific methylation reagents. The challenges of mono N‐methylation of aliphatic amines and N‐methylation of peptides are discussed. This review will be useful for chemists wanting to select the appropriate reagents for methylation chemistry. Based on the large diversity of methylation reagents and their wide scope, this review also broadens perspectives on which strategies to select for utilizing a particular methylation, resulting in an increased flexibility in synthetic route planning.

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“…Again using cinnamic acids, Mao and co-workersd escribed an FeCl 3 (20 mol %)-catalyzed decarboxylativem ethylation reaction in the presence of di-tert-butylperoxide (2 equiv). [51] Through investigations with deuterated solvents, it was established that di-tert-butylperoxide was the source of the methyl radical, which added to the cinnamic acids ubstrate to afford aradicalintermediate that underwent decarboxylation and oxidation to give the methylated alkene in at ypeD mechanism.…”

Section: Radical-mediated Formation Of Càcb Onds By Iron(iii)mentioning

confidence: 99%

Iron‐Promoted Radical Reactions: Current Status and Perspectives

2017

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Catalysis based on precious metals has reached an incredible level of sophistication and has found widespread use and application,b oth in academia andi ni ndustry.H owever,o wing to the environmental impact, cost, and low abundance, catalysis based on inexpensive, abundant,a nd environmentally benign first-row transition metals has become av aluable alternative to traditional reactions promoted by their less-abundantc ounterparts. From economic and ecological perspectives, iron salts and iron metal complexes are highly promising candidates to replace costly and toxic metals. In recent years, iron complexes have been used to promote the formation of radicals. Photoredox chemistry is av aluablem ethod for the generation of radical species under mild conditions, but it often relies on rare-earth-metal complexes.T he employment of iron complexes for the generation of radicals is attractive for the development of sustainable, simple, and effective procedures.I nt his Focus Review,w eh ighlight and summarize recent radicalr eactions promoted by iron complexes and their application in organic reactions.

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Iron-catalyzed decarboxylative methylation of α,β-unsaturated acids under ligand-free conditions

Cited by 41 publications

References 33 publications

Iron Catalysis in Organic Synthesis

Iron Catalysis in Organic Synthesis

Recent Advances in Methylation: A Guide for Selecting Methylation Reagents

Iron‐Promoted Radical Reactions: Current Status and Perspectives

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