Catalytic activity of gold nanoclusters in intramolecular hydroamination of alkenes and alkynes with toluenesulfonamide under aerobic and basic conditions

Kitahara, Hiroaki; Sakurai, Hidehiro

doi:10.1016/j.jorganchem.2010.08.038

Cited by 34 publications

(17 citation statements)

References 41 publications

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“…High enantioselectivities were achieved in the asymmetric intramolecular hydroamination of allenes by using a variety of chiral phosphine–Au(I) complexes [57–63]. On the other hand, the intramolecular hydroamination of olefins is a more important reaction in organic synthesis and has been widely reported [64–68]. Recently, the enantioselective intramolecular hydroamination of olefins has also been significantly improved by using various transition metal complexes or other metal complexes [69–77].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses

Sun¹,

Xu²,

Shi³

2013

Beilstein J. Org. Chem.

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Several novel chiral N-heterocyclic carbene and phosphine ligands were prepared from (S)-BINOL. Moreover, their ligated Au complexes were also successfully synthesized and characterized by X-ray crystal diffraction. A weak gold-π interaction between the Au atom and the aromatic ring in these gold complexes was identified. Furthermore, we confirmed the formation of a pair of diastereomeric isomers in NHC gold complexes bearing an axially chiral binaphthyl moiety derived from the hindered rotation around C-C and C-N bonds. In the asymmetric intramolecular hydroamination reaction most of these chiral Au(I) complexes showed good catalytic activities towards olefins tethered with a NHTs functional group to give the corresponding product in moderate yields and up to 29% ee. 2224

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Section: Resultsmentioning

confidence: 99%

Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses

Sun¹,

Xu²,

Shi³

2013

Beilstein J. Org. Chem.

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“…Gold complexes have emerged as highly active catalysts for the hydroamination of unsaturated carbon-carbon bonds [21][22][23]. While reactions involving nucleophilic additions to more reactive alkynes and allenes are well established, only more recently have unactivated alkenes participated in gold-catalyzed hydroamination reactions [24].…”

Section: Gold-catalyzed Reactionsmentioning

confidence: 99%

Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Hydroamination or Hydroalkoxylation Reactions

Julian

2013

Topics in Heterocyclic Chemistry

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The intramolecular hydrofunctionalization of carbon-carbon multiple bonds has emerged as a powerful way to form cyclic structures. A particularly important class of reactions involves the use of amine or alcohol nucleophiles, and alkenes or allenes as electrophiles, to form pyrrolidine, piperidine, tetrahydrofuran, and tetrahydropyran heterocycles in a highly efficient manner using late transition metal catalysts. Asymmetric methods for hydroamination and hydroalkoxylation reactions have recently emerged, allowing for the enantioselective synthesis of such saturated heterocycles. This review covers recent developments (over the last 5-10 years) in late transition metal-catalyzed hydroamination and hydroalkoxylation reactions that generate saturated heterocycles.

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“…For the related hydroamination processes, a similar reaction mechanism was postulated. [98][99][100] DFT calculations were also applied to investigate the structure, reactivity, and catalytic activity in n-alkane hydroisomerization of model Pt 6 particles encapsulated in different zeolites. [124][125][126] The results show that interaction of the platinum particle with the acid sites of the support suppresses both its Lewis and Brønsted acidities.…”

Section: Insight On Mechanistic Aspectsmentioning

confidence: 99%

Nanocatalysts for Rearrangement Reactions

García‐Álvarez

García‐Garrido

Cadierno

2013

Nanocatalysis Synthesis and Applications

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Catalytic activity of gold nanoclusters in intramolecular hydroamination of alkenes and alkynes with toluenesulfonamide under aerobic and basic conditions

Cited by 34 publications

References 41 publications

Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses

Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses

Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Hydroamination or Hydroalkoxylation Reactions

Nanocatalysts for Rearrangement Reactions

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