Au(I)-Catalyzed Highly Efficient Intermolecular Hydroamination of Alkynes

Mizushima, Eiichiro; Hayashi, Teruyuki; Tanaka, Masato

doi:10.1021/ol0353159

Cited by 296 publications

(155 citation statements)

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“…Subsequently, gold(III) complexes were investigated as catalysts and used in the synthesis of five-membered rings with two heteroatoms [15][16][17][18]. Several years later, R 3 PAuX (X = trifluoromethanesulphonate, OTf − ) or other weakly coordinating counter ions) demonstrated excellent catalytic performance in Conia-ene [19,20] and hydroarylation [21][22][23] reactions, as well as several carbon-heteroatom bond-forming reactions [24][25][26]. Recently, Zhang's group designed a new complex with the ligand (1,1 -biphenyl)-2-ylphosphine, which was found to be effective in the reaction of acid and alkynes with a turnover number up to 99,000 [27].…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient One-Pot Synthesis of 2,4-Disubstituted Thiazoles Using Au(I) Catalyzed Oxidation System at Room Temperature

Wang

Líu

2016

Catalysts

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Abstract:In the present work, gold complex catalysts with Mor-DalPhos ligands were successfully prepared using mesylates as counter ions. Seven ammonium sulfonates were synthesized to promote the production of intermediate sulfonyloxymethyl ketone. It was found that low-acidity N,N-dimethylbenzenaminium methanesulfonate showed excellent activity in the reaction. Furthermore, the catalysts effectively avoided the loss of activity due to the low acidity. Various thioamides were directly added to the resulting reaction mixture without the separation of intermediate product. Then, twenty kinds of 2,4-disubstituted thiazoles were efficiently synthesized at room temperature with the highest yield of 91%. This work provides an efficiency and mild gold-catalyzed oxidation system for the one-pot synthesis of thiazole and its derivatives.

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Section: Introductionmentioning

confidence: 99%

Highly Efficient One-Pot Synthesis of 2,4-Disubstituted Thiazoles Using Au(I) Catalyzed Oxidation System at Room Temperature

Wang

Líu

2016

Catalysts

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“…Um mecanismo possível para essa transformação se baseia na proposta de Mizushima, Hayashi e Tanaka, 17 Até então, apenas condições drásticas haviam sido utilizadas para a reação de hidroaminação com amônia. Um exemplo é a utilização de uma mistura de etileno e amônia em temperaturas superiores a 170 °C e pressões acima de 800 bar com sódio metálico catalítico para gerar uma mistura de etilamina, dietilamina e trietilamina.…”

Section: Hidroaminação Com Amôniaunclassified

“…O pré-catalisador Cp 2 TiMe 2 (17) foi empregado na síntese total do alcaloide (−)-xilopinina por Mujahidin e Doye. 22,23 A partir do composto 27 foi realizada uma hidroaminação intramolecular para gerar a imina 28, após tautomerização.…”

Section: Uso De Aminas Primárias: Metais Do Grupounclassified

Avanços recentes na hidroaminação de compostos insaturados

Novaes¹,

Pastre²

2017

Quim. Nova

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publicado na web em 16/05/2017 RECENT ADVANCES ON HYDROAMINATION OF UNSATURATED COMPOUNDS. This review presents thermodynamics and kinetics aspects of the hydroamination reaction, recent advancements on this field for non-activated alkenes, alkynes and allenes, employing transition metal catalysis or organocatalysis, including activation by hydrogen bonding or Brønsted acids. Selected syntheses that contain a strategic hydroamination step will be discussed, and advancements on the asymmetric version will also be highlighted. The full coverage of scientific activity about hydroamination is beyond this review, therefore the examples presented are from the last ten years, except when there are historical reasons for the discussion of previous works.

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“…NMR experiments have shown that even an excess of BF 3 [79]. The hydroarylation of alkynyl(methyl)ketones to give arylvinyl(methylketones) has been accomplished using [(Ph 3 P)AuCl] and BF 3 · OEt 2 in nitromethane [80].…”

Section: Activation Of Complexes [(L)aux] With Lewis Acidsmentioning

confidence: 99%

Silver-free Gold(I) Catalysts for Organic Transformations

Schmidbaur

Schier

2011

Zeitschrift Für Naturforschung B

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The majority of gold(I) catalysts employed in organic transformations in homogeneous systems are presently generated in situ by reactions of gold halides AuX or their 1 : 1 complexes [(L)AuX] with silver salts AgY (X = Cl, Br; L = R 3 P, NHC, tht etc.; Y = BF 4 , PF 6 , SbF 6 , OSO 2 CF 3 , OC(O)CF 3 etc.). This usage of silver salts is not only economically unfavorable, but also has several practical disadvantages regarding inter alia the thermal and photochemical stability of the reaction mixtures, problems of inexact stoichiometries, difficulties in separation and recycling, and cooperative effects due to Au-Ag metallophilic interactions which can induce a different course of the reactions. There is therefore a move towards syntheses of silver-free homogeneous gold(I) catalysts. The past and current approaches and opportunities are summarized in this review.

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Au(I)-Catalyzed Highly Efficient Intermolecular Hydroamination of Alkynes

Abstract: [reaction: see text] Addition of aniline derivatives to aromatic and aliphatic alkynes proceeds efficiently in the presence of a gold(I) catalyst (0.01-1.0 mol %) to afford ketimines in good yields

Cited by 296 publications

References 43 publications

Highly Efficient One-Pot Synthesis of 2,4-Disubstituted Thiazoles Using Au(I) Catalyzed Oxidation System at Room Temperature

Highly Efficient One-Pot Synthesis of 2,4-Disubstituted Thiazoles Using Au(I) Catalyzed Oxidation System at Room Temperature

Avanços recentes na hidroaminação de compostos insaturados

Silver-free Gold(I) Catalysts for Organic Transformations

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