Iron‐Catalyzed Amidation of Aldehydes with <i>N</i>‐Chloroamines

Porcheddu, Andrea; Luca, Lidia De

doi:10.1002/adsc.201200659

Cited by 48 publications

(26 citation statements)

References 45 publications

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“…The quaternary ammonium salt will provide an amino radical24 in the presence of Fe 2+ . Coupling of the acyl radical and the amino radical should yield the product amide 25…”

Section: Resultsmentioning

confidence: 99%

Iron‐Catalyzed Direct Synthesis of Amides from Methylarenes

2015

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An efficient, green and first catalytic process hasb een developed for the direct synthesiso f amides from readilya vailablep etroleum by-products (methylarenes) anda mines using an iron catalyst. In this newc atalytic reaction, the methylg roup of the methylarene is oxidized to the corresponding aldehyde through non-directed C (sp 3 ) À Ho xidation followed by its oxidative amidation with N-chloroamine,y ielding the carboxylic amide.O xidation with an iron catalyst, tert-butyl hydroperoxide (TBHP) as sole oxidant, the synthesiso fa mides under mild reaction conditions and the utilizationo fm ethylarenes as starting material maket his methodology novel and environmentally benign.

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“…The quaternary ammonium salt will provide an amino radical24 in the presence of Fe 2+ . Coupling of the acyl radical and the amino radical should yield the product amide 25…”

Section: Resultsmentioning

confidence: 99%

Iron‐Catalyzed Direct Synthesis of Amides from Methylarenes

2015

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“…chloroamines 101,a nd TBHP in MeCN (Scheme 41). [85] Both aliphatic and aromatic aldehydes were successfully tolerated in this procedure, with secondary andt ertiary chloroamines.T he reactions tarts with the oxidation of tBuOOH into the tBuOOC radicalb yF e III .T his radical species is able to abstract ah ydrogen radical from RCHO. The resulting RCOC species couples with the amine radical cation that is obtained from chloramine by reduction with Fe II .…”

Section: Radical-mediated Addition To C=xbonds By Iron(iii)mentioning

confidence: 93%

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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“…In order to find cost-effective and with a broad substrate scope procedures we have studied the possibility to replace expensive transition metal catalysts with salts of more environmental benign and cheap metals. In this contest we have reported 24 a new direct conversion of aldehydes to amides, in the presence of iron(III) chloride as a catalyst and TBHP as an oxidant (Scheme 19). The iron catalysis appears very appealing due to its relative non-toxicity, easy availability and low price, especially compared with catalysis based on precious metals.…”

Section: Metal Catalysed Amidation Of Aldehydesmentioning

confidence: 97%