Ni-Catalyzed Direct Reductive Amidation via C–O Bond Cleavage

Correa, Arkaitz; Martı́n, Rubén

doi:10.1021/ja5029793

Cited by 140 publications

(39 citation statements)

References 80 publications

(31 reference statements)

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“…Transmetalation to zinc followed by protonolysis furnishes the amide product. This sequence bears some resemblance to Ni-catalysed reductive coupling of carbon electrophiles with isocyanates to form amides3031.…”

Section: Resultsmentioning

confidence: 91%

Direct amidation of esters with nitroarenes

2017

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Esters are one of the most common functional groups in natural and synthetic products, and the one-step conversion of the ester group into other functional groups is an attractive strategy in organic synthesis. Direct amidation of esters is particularly appealing due to the omnipresence of the amide moiety in biomolecules, fine chemicals, and drug candidates. However, efficient methods for direct amidation of unactivated esters are still lacking. Here we report nickel-catalysed reductive coupling of unactivated esters with nitroarenes to furnish in one step a wide range of amides bearing functional groups relevant to the development of drugs and agrochemicals. The method has been used to expedite the syntheses of bio-active molecules and natural products, as well as their post-synthetic modifications. Preliminary mechanistic study indicates a reaction pathway distinct from conventional amidation methods using anilines as nitrogen sources. The work provides a novel and efficient method for amide synthesis.

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Section: Resultsmentioning

confidence: 91%

Direct amidation of esters with nitroarenes

2017

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“…In 2014, Correa and Martin developed an efficient Ni-catalyzed reductive coupling method to amides by exposure of aryl electrophiles to isocyanates (Scheme 38) [98]. The competence of C(sp 2 )-O and C(sp 3 )-O electrophiles for amide synthesis significantly expands the source of electrophiles other than halides, since naphthyl and naphthalen-2-ylmethyl pivalates as well as aryl tosylates are suitable.…”

Section: Coupling Of Aryl Electrophiles With Carbonyl Compoundsmentioning

confidence: 99%

Nickel-Catalyzed Reductive Couplings

2016

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The Ni-catalyzed reductive coupling of alkyl/aryl with other electrophiles has evolved to be an important protocol for the construction of C-C bonds. This chapter first emphasizes the recent progress on the Ni-catalyzed alkylation, arylation/vinylation, and acylation of alkyl electrophiles. A brief overview of CO2 fixation is also addressed. The chemoselectivity between the electrophiles and the reactivity of the alkyl substrates will be detailed on the basis of different Ni-catalyzed conditions and mechanistic perspective. The asymmetric formation of C(sp(3))-C(sp(2)) bonds arising from activated alkyl halides is next depicted followed by allylic carbonylation. Finally, the coupling of aryl halides with other C(sp(2))-electrophiles is detailed at the end of this chapter.

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“…We also briefly explored the possibility of a reductive coupling between an aryl halide and an isocyanate using our conditions. Indeed, this transformation has only been reported under Ni catalysis . As an illustrative example, we submitted a mixture of bromide 1 g‐Br and phenyl isocyanate 9 to the Co II /Zn catalytic system and were delighted to isolate the expected amide 10 in a promising 66 % yield (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Co^I‐Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines

Presset

Paul

Cherif

et al. 2019

Chemistry A European J

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The reductive Barbier coupling of aromatic halides and electrophiles has been achieved using a CoBr2/1,10‐phenanthroline catalytic system and over stoichiometric amounts of zinc. The reaction displayed a broad scope of substrates, including (hetero)aryl chlorides as pro‐nucleophiles and aldehydes or imines as electrophiles, leading to diarylmethanols and diarylmethylamines in moderate to excellent yields, respectively.

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Ni-Catalyzed Direct Reductive Amidation via C–O Bond Cleavage

Cited by 140 publications

References 80 publications

Direct amidation of esters with nitroarenes

Direct amidation of esters with nitroarenes

Nickel-Catalyzed Reductive Couplings

Co^I‐Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines

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Ni-Catalyzed Direct Reductive Amidation via C–O Bond Cleavage

Cited by 140 publications

References 80 publications

Direct amidation of esters with nitroarenes

Direct amidation of esters with nitroarenes

Nickel-Catalyzed Reductive Couplings

CoI‐Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines

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Product

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About

Co^I‐Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines