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1.
J Org Chem ; 2024 Aug 30.
Artigo em Inglês | MEDLINE | ID: mdl-39213645

RESUMO

With the assistance of nickel as catalyst, 2,2'-bipyridine (bpy) as ligand, and manganese as reducing metal, the reductive amidation of isocyanates with readily accessible aryl fluorosulfates could be successfully accomplished. The reactions proceeded effectively via C-O bond activation in DMF at room temperature, enabling the facile synthesis of a range of structurally diverse amides in moderate to high yields with broad functionality compatibility. In addition, the synthetic usefulness of the method was further demonstrated by applying the reaction in scale-up synthesis and the late-stage functionalization of complex molecules with biological activities.

3.
Org Lett ; 26(1): 416-420, 2024 Jan 12.
Artigo em Inglês | MEDLINE | ID: mdl-38160397

RESUMO

A reductive amidation of triazine esters with nitroarenes by using cheap iron as a reducing metal in the presence of TMSCl in DMF was developed. The reactions proceeded efficiently under transition metal-free conditions to give the corresponding amides in moderate to good yields with good functional group compatibility. Preliminary mechanistic investigations indicated that nitrosobenzene, N-phenyl hydroxylamine, azoxybenzene, azobenzene, aniline, and N-arylformamide possibly served as the intermediates of the reaction.

4.
Org Lett ; 25(29): 5525-5529, 2023 Jul 28.
Artigo em Inglês | MEDLINE | ID: mdl-37459275

RESUMO

A nickel-catalyzed direct cross-coupling of unactivated aryl fluorides with aryl bromides is realized. The one-pot reaction, which avoids the use of preformed and sensitive organometallic reagents, proceeds effectively via C-F bond cleavage at room temperature in THF in the presence of the phosphine ligand and magnesium powder (with or without TMSCl) to produce the desired biaryls in modest to good yields.

5.
Org Lett ; 25(10): 1771-1775, 2023 Mar 17.
Artigo em Inglês | MEDLINE | ID: mdl-36862539

RESUMO

A straightforward cross-coupling of aryl thioether with aryl bromide with the aid of nickel salt, magnesium, and lithium chloride in tetrahydrofuran at ambient temperature was accomplished. The one-pot reactions proceeded efficiently via C-S bond cleavage to produce the desired biaryls in modest to good yields, avoiding the use of pregenerated or commercial organometallic reagents.

6.
Org Lett ; 25(13): 2318-2322, 2023 Apr 07.
Artigo em Inglês | MEDLINE | ID: mdl-36961113

RESUMO

A one-pot, direct cross-coupling of aryl fluorosulfate with aryl bromide, which is step-economical and avoids the use of a preprepared/commercial organometallic reagent, could be accomplished by performing the reaction in THF at room temperature in the presence of nickel catalyst, magnesium turnings, and lithium chloride, giving rise to the corresponding biaryls in moderate to good yields with reasonable functional group compatibility.

7.
J Org Chem ; 87(17): 11899-11908, 2022 Sep 02.
Artigo em Inglês | MEDLINE | ID: mdl-35957561

RESUMO

The direct cross-couplings of diaryl sulfoxides with aryl bromides via C-S bond cleavage could be readily accomplished using nickel(II) as the catalyst, 1,2-bis(diphenylphosphino)ethane (dppe) as the ligand, and magnesium turnings as the reducing metal in THF, leading to the corresponding biaryls in moderate to good yields. The reaction exhibited a broad substrate scope and could be applied to a gram-scale synthesis. The "one-pot" reaction, which avoids the utility of presynthesized and moisture-labile organometallic compounds, is operationally simple and step-economic.

8.
Org Lett ; 24(10): 1953-1957, 2022 Mar 18.
Artigo em Inglês | MEDLINE | ID: mdl-35244408

RESUMO

The direct cross-couplings of aryl sulfonium salts with aryl halides could be achieved by using nickel as a reaction catalyst. The reactions proceeded efficiently via C-S bond activation in the presence of magnesium turnings and lithium chloride in THF at ambient temperature to afford the corresponding biaryls in moderate to good yields, potentially serving as an attractive alternative to conventional cross-coupling reactions employing preprepared organometallic reagents.

9.
Org Lett ; 23(13): 5118-5122, 2021 Jul 02.
Artigo em Inglês | MEDLINE | ID: mdl-34160224

RESUMO

A nickel-catalyzed direct reductive cross-coupling of disubstituted cycloalkyl iodides with aryl iodides was developed. The one-pot reaction, which is simple to operate, was capable of proceeding efficiently in a stereocontrolled manner to afford a variety of cross-coupled products with high diastereoselectivity and wide functional group tolerance.

10.
Org Lett ; 21(15): 5873-5878, 2019 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-31318222

RESUMO

An efficient, economical, and practical Reformatsky reaction of α-halo carbonyl compounds with aldehydes/ketones by using cheap and commercial iron(0) powder as reaction mediator is developed. The reactions proceeded effectively in the presence of a catalytic amount of iodine (20 mol %) to afford the synthetically useful ß-hydroxyl carbonyl compounds in moderate to good yields.

11.
Org Lett ; 16(3): 956-9, 2014 Feb 07.
Artigo em Inglês | MEDLINE | ID: mdl-24479467

RESUMO

Chloro-substituted triethylsilyl enol ethers derived from cyclohexanone and related ketones are converted with aluminum powder in the presence of indium trichloride to functionalized allylic aluminum reagents which represent a new type of synthetic equivalent of metal enolates. These allylic organometallics undergo highly diastereoselective additions to aldehydes and methyl aryl ketones, giving aldol products with a ß-quaternary center.


Assuntos
Alumínio/química , Cicloexanonas/química , Éteres/química , Indicadores e Reagentes/química , Compostos Organometálicos/química , Compostos de Organossilício/química , Estrutura Molecular , Estereoisomerismo
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