A5069786510- Catalytic C–H Functionalization Methods
- Sulfur-Based Synthesis Techniques
- Radical Photochemical Reactions
- Cyclopropane Reaction Mechanisms
- Catalytic Alkyne Reactions
- Synthetic Organic Chemistry Methods
- Catalytic Cross-Coupling Reactions
- N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
- Asymmetric Synthesis and Catalysis
- Organoboron and organosilicon chemistry
- Oxidative Organic Chemistry Reactions
- Organometallic Complex Synthesis and Catalysis
- Advanced Synthetic Organic Chemistry
The Ohio State University
2021-2024
Heidelberg University
2018-2020
Shanghai Institute of Organic Chemistry
2016
Chinese Academy of Sciences
2016
Abstract While gold‐mediated synergistic catalytic processes involving transmetalations with other metals are well understood, Au I /Au III cycles in these reactions rarely reported. Herein a gold‐catalyzed direct alkynylation of cyclopropenes is enabled by two operating cycles, an oxidative cycle alkynyl complex formed addition and one silver‐mediated C−H activation.
Abstract Herein we report a highly selective photoredox C(sp 3 )−H alkylation/arylation of ethers through the combination photo‐organocatalyst (benzaldehyde) and transition‐metal catalyst (nickel). This method provides simple general strategy for ethers. A late‐stage modification (−)‐ambroxide has also been conducted to demonstrate applicability method.
Geminal diboronates have attracted significant attention because of their unique structures and reactivity. However, benzofuran-, indole-, benzothiophene-based benzylic gem-diboronates, building blocks for biologically relevant compounds, are unknown. A promising protocol using visible light aryl iodides constructing valuable blocks, including via radical carbo-cyclization/gem-diborylation alkynes with a high functional group tolerance is presented. The utility these gem-diboronates has been...
A cross-selective aza-pinacol coupling of aldehydes and imines has been developed to afford valuable β-amino alcohols. This strategy enables chemoselective conversion aliphatic ketyl radicals, in the presence more easily reduced other functional groups. Upon carbonyl-specific activation by AcI, a photoinitiated Mn catalyst selectively reduces resulting α-oxy iodide an atom transfer mechanism. The ensuing radical couples imines, precluding homodimerization classical reductive approach. In...
Carbenes are highly enabling reactive intermediates that facilitate a diverse range of otherwise inaccessible chemistry, including small-ring formation and insertion into strong σ bonds. To access such valuable reactivity, reagents with high entropic or enthalpic driving forces often used, explosive (diazo) unstable ( gem -dihalo) compounds. Here, we report common aldehydes readily converted (via stable α-acyloxy halide intermediates) to electronically (donor neutral) carbenes >10...
[Au2(μ-dppm)2]Cl2-mediated photocatalysis reactions are usually initiated by ultraviolet A (UVA) light; herein, an unreported system using blue light-emitting diodes (LEDs) as excitation light source was found. The red shift of the absorption wavelength originates from combination [Au2(μ-dppm)2]Cl2 and ligand (Ph3P or mercaptan). On basis this finding, a gold-catalyzed reductive desulfurizing C–C coupling electrophilic radicals styrenes mediated LEDs is presented, which cannot be efficiently...
Herein a synergistic combination of nickel catalyst and benzaldehyde for the utilization amides thioethers in C(sp3)–H alkylation arylation reactions employing simple aryl or alkyl halides is reported. This method provides cheap strategy direct functionalization thioethers. Readily available starting materials, mild reaction conditions, good functional-group tolerance, broad substrate scope make this methodology attractive practical pharmaceutical synthetic chemistry.
Saturated heterocyclic acetals are useful fragments in organic synthesis and other fields. Herein, C(sp3)–H dehydrogenative cross-couplings of ethers, tetrahydrothiophenes, pyrrolidines were achieved under visible light irradiation by using iodobenzene an situ-formed gold complex. The broad functional group compatibility substrate scope indicate that our strategy is a promising way to synthesize acetal analogues. method was successfully applied late-stage modifications bioactive molecules....
An Oppolzer's sultam-based highly stereoselective α-hydroxylation of amides was developed to deliver the desired products in good yield and excellent diastereoselectivity (>20/1). The generally crystalline recyclability chiral auxiliary illustrate practicability scalability current approach.
Cyclopropanes are ubiquitous in medicines, yet robust synthetic access to a wide range of sterically and electronically diverse analogs remains challenge. To address the limitations most direct strategy, (2+1) cycloaddition, we sought develop variant that employs non-stabilized carbenes. We present herein an FeCl2-catalyzed cyclopropanation uniquely aliphatic (enolizable) aldehydes as carbene precursors. A remarkably broad alkenes may be coupled with these non-stabilized, alkyl This...