Asymmetric synthesis of N-allylic indoles via regio- and enantioselective allylation of aryl hydrazines

Xu, Kun; Gilles, Thomas; Breit, Bernhard

doi:10.1038/ncomms8616

Cited by 89 publications

(21 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Furthermore, a related substrate structure, arylhydrazine 153, was successfully coupled with terminal allene 148 using the Rh(I)/(S)-DTBM-Segphos (S)-L10 or Rh(I)/(S)-DTBM-BINAP (S)-L13 catalyst systems followed by Fischer indolization to afford the enantioenriched N-allylindoles 154 in good yields and with high N 1 selectivity. 52 This onepot, two-step procedure represents the first asymmetric route towards branched N-allylic indoles via Rh-catalyzed C-N coupling with an allene using arylhydrazines (Table 3, entry 2). The more acidic N-H bond at N 1 drives the faster oxidative addition in preference to the less acidic N-H at N 2 .…”

Section: Syn Thesismentioning

confidence: 99%

Rhodium-Catalyzed Allylation Reactions

Thoke

Kang

2019

Synthesis

View full text Add to dashboard Cite

Rhodium-catalyzed allylation reactions are well known for their unique selectivity and reactivity due to the high memory effect of Rh as compared to other metals. These reactions involve the substitution of allylic rhodium intermediates with a diverse range of different nucleophiles, leading to C–C and C–heteroatom bond formation. Modern organic chemists are, however, interested in atom-economical protocols under greener pathways and following recent increased understanding of mechanistic aspects of Rh-catalyzed allylation via the hydrofunctionalization of allenes or alkynes, great strides have made in the design and development of new atom-economical protocols. In this article, we review this field from its beginning to current state.1 Introduction2 Rhodium-Catalyzed Allylic Substitution3 Rhodium-Catalyzed Allylation with Allenes4 Rhodium-Catalyzed Allylation with Alkynes5 Rhodium-Catalyzed Allylation with Dienes6 Rhodium-Catalyzed Allylation by ARO of Oxabicyclic Alkenes7 Rhodium-Catalyzed Enantioselective Allylation in Natural Product and Drug Synthesis8 Conclusion

show abstract

Section: Syn Thesismentioning

confidence: 99%

Rhodium-Catalyzed Allylation Reactions

Thoke

Kang

2019

Synthesis

View full text Add to dashboard Cite

show abstract

“…Qi et al [35] synthesized porous nickel-iron oxide via co-precipitation reaction at 60°C, which exhibited highly efficient OER performance. Lu et al [36] prepared amorphous NiFe hydroxide nanosheets on Ni foam via electrodeposition as efficient OER electrode. However, all these approaches require extra energy replenishment, which costs a lot and runs counter to green energy.…”

Section: Introductionmentioning

confidence: 99%

Green synthesis of NiFe LDH/Ni foam at room temperature for highly efficient electrocatalytic oxygen evolution reaction

et al. 2018

View full text Add to dashboard Cite

Clean energy technologies such as water splitting and fuel cells have been intensively pursued in the last decade for their free pollution. However, there is plenty of fossil energy consumed in the preparation of the catalysts, which results in a heavy pollution. Therefore, it is much desired but challenging to fabricate high-efficiency catalysts without extra energy input. Herein, we used a facile one-pot room-temperature method to synthesize a highly efficient electrocatalyst of nickel iron layered double hydroxide grown on Ni foam (NiFe LDH/NF) for oxygen evolution reaction (OER). The formation of the NiFe LDH follows a dissolutionprecipitation process, in which the acid conditions by hydrolysis of Fe 3+ combined with NO 3 − could etch the NF to form Ni 2+. Then, the obtained Ni 2+ was co-precipitated with the hydrolysed Fe 3+ to in situ generate NiFe LDH on the NF. The NiFe LDH/NF exhibits excellent OER performance with a low potential of about 1.411 V vs. reversible hydrogen electrode (RHE) at a current density of 10 mA cm −2 , a small Tafel slope of 42.3 mV dec −1 and a significantly low potential of~1.452 V vs. RHE at 100 mA cm −2 in 1 mol L −1 KOH. Moreover, the material also keeps its original morphology and structure over 20 h. This energy-efficient strategy to synthesize NiFe LDH is highly promising for widespread application in OER catalyst industry.

show abstract

“…Metal oxides with complex structures or rich morphologies have recently been explored for catalytic oxidation applications. Examples include Co 3 O 4 nanorods, Co 3 O 4 /graphene nanocomposites, integrated spinel nanoarrays, interfacial Pt-NiO 1-x nanostructures, Pt@mSiO 2 core-shell nanospheres, and nickel-iron foams (Xie et al., 2009, Lu and Zhao, 2015, Ren et al., 2014, Liang et al., 2011, Joo et al., 2009, Kim et al., 2018, Wang et al., 2012). Our present design of bimetallic spinel oxide multi-shelled hollow microspheres with wide tailorability and functionality enables the reactive molecules to directly enter their interior space by offering more open channels and less diffusion obstruction so as to take full advantage of highly exposed active sites and enhanced synergetic effect of components in such mixed metal oxides.…”

Section: Resultsmentioning

confidence: 99%

“…The hollow micro- or nanostructures with controllable size, shape, composition, and interior architecture have important implications in vast fields (Hu et al., 2011, Li and Shi, 2014, Dai et al., 2015, Li et al., 2016b). Encouraged by the observation on building novel 3D nanostructures such as foams and urchins to overcome the structure collapsing problems (Lu and Zhao, 2015, You et al., 2016), we go forward to think that it a feasible strategy to design spinel oxide systems on the basis of forming robust multi-shelled hollow microsphere structure to enhance the catalytic activity and stability during long-term oxidation process. Meanwhile, largely due to the water strongly binding to metal-oxygen sites, monometallic catalysts often suffer severely from water poisoning at low temperature (Goodman et al., 2017).…”

Section: Introductionmentioning

confidence: 99%

Template-free Synthesis of Stable Cobalt Manganese Spinel Hollow Nanostructured Catalysts for Highly Water-Resistant CO Oxidation

Zhang

et al. 2019

iScience

View full text Add to dashboard Cite

SummaryDevelopment of spinel oxides as low-cost and high-efficiency catalysts is highly desirable; however, rational synthesis of efficient and stable spinel systems with precisely controlled structure and components remains challenging. We demonstrate the design of complex nanostructured cobalt-based bimetallic spinel catalysts for low-temperature CO oxidation by a simple template-free method. The self-assembled multi-shelled mesoporous spinel nanostructures provide high surface area (203.5 m2/g) and favorable unique surface chemistry for producing abundant active sites and lead to the creation of robust microsphere configured by 16-nm spinel nanosheets, which achieve satisfactory water-resisting property and catalytic activity. Theoretical models show that O vacancies at exposed {110} facets in cubic spinel phase guarantee the strong adsorption of reactive oxygen species on the surface of catalysts and play a key role in the prevention of deactivation under moisture-rich conditions. The design concept with architecture and composition control can be extended to other mixed transition metal oxide compositions.

show abstract

Asymmetric synthesis of N-allylic indoles via regio- and enantioselective allylation of aryl hydrazines

Cited by 89 publications

References 54 publications

Rhodium-Catalyzed Allylation Reactions

Rhodium-Catalyzed Allylation Reactions

Green synthesis of NiFe LDH/Ni foam at room temperature for highly efficient electrocatalytic oxygen evolution reaction

Template-free Synthesis of Stable Cobalt Manganese Spinel Hollow Nanostructured Catalysts for Highly Water-Resistant CO Oxidation

Contact Info

Product

Resources

About