A highly luminescent three-dimensional microporous metal-organic framework, [Zn(2)(oba)(2)(bpy)]·DMA, demonstrates unique selectivity for the detection of high explosives and other aromatics via a fluorescence quenching enhancement mechanism.

An intramolecular dearomatization of indole derivatives based on visible-light-promoted [2+2] cycloaddition was achieved via energy transfer mechanism. The highly strained cyclobutane-fused angular tetracyclic spiroindolines, which were typically unattainable under thermal conditions, could be directly accessed in high yields (up to 99%) with excellent diastereoselectivity (>20:1 dr) mild conditions. method also compatible diverse functional groups and amenable flexible transformations. In...

Exploring the enormous chemical space through an expedient building-up of molecular diversity is important goal organic chemistry. The development synthetic methods toward molecules with unprecedented structural motifs lays foundation for wide applications ranging from pharmaceutical chemistry to materials science. In this regard, dearomatization arenes has been recognized as a unique strategy since it provides novel retrosynthetic disconnections various spiro or fused polycyclic increased...

A convenient approach to selectively prepare a wide range of functionalized propiolic acids was developed by AgI-catalyzed carboxylation terminal alkynes using carbon dioxide as carboxylative agent under ligand-free conditions.

An Ir-catalyzed intermolecular asymmetric dearomatization reaction of substituted indoles with allylic alcohols has been realized to afford the corresponding indoline derivatives in 71–97% yield up 98% ee presence Lewis acid Fe(OTf)2. This methodology features enantioselective construction all-carbon quaternary stereogenic centers prochiral nucleophiles and its utility demonstrated total synthesis (−)-debromoflustramine B.

Chiral phosphoric acid worked together with Hoveyda–Grubbs II catalyst enabling highly efficient synthesis of enantioenriched tetrahydro-β-carbolines (up to 98% yield, 99% ee) through a ring-closing metathesis/isomerization/Pictet–Spengler cascade reaction via sequential catalysis.

A ligand-enabled Ir-catalyzed diastereoselective and enantioselective allylic alkylation of 3-substituted indoles is reported, providing indoline products containing three contiguous stereocenters in one step with high site-, regio-, diastereo- enantioselectivities from a wide range readily available starting materials.

Abstract Presented here is a class of novel axially chiral aryl‐ p ‐quinones as platform molecules for the preparation non‐ C 2 symmetric biaryldiols. Two sets ‐quinone frameworks were synthesized with remarkable enantiocontrol by means phosphoric acid catalyzed enantioselective arylation central‐to‐axial chirality conversion. These then used to access wide spectrum highly functionalized biaryldiols excellent retention enantiopurity.

An intramolecular dearomatization of indole derivatives has been developed via an electron donor–acceptor complex formed between and Umemoto's reagent. Without the requirement any catalyst additive, diverse trifluoromethyl-substituted spiroindolenines bearing a quaternary stereogenic center were obtained in good yields (up to 90%) merely upon illumination two starting materials 1,2-dichloroethane solution at room temperature. This work provides facile access trifluoromethyl group enabled by...

Abstract Herein we report visible‐light‐induced intramolecular double dearomative cycloaddition of arenes. Compared with the well‐known photodimerization arenes under ultraviolet irradiation, current reactions are carried out mild conditions and feature wide substrate scope. A large array structurally‐diverse polycyclic indoline derivatives is afforded in high yields (up to 98 %) exclusive diastereoselectivity (>20:1 dr) via [4+2] or [2+2] pathway.

An electroreductive arylation reaction of aliphatic and aromatic aldehydes as well ketones with electro-deficient (hetero)arenes is described. A variety cyano(hetero)arenes carbonyl compounds, especially aldehydes, have been examined, providing secondary tertiary alcohols in moderate to good yields. Mechanistic studies, including cyclic voltammetry (CV), electron paramagnetic resonance (EPR), divided-cell experiments, support the generation ketyl radicals persistent heteroaryl radical anions...

Abstract The first iridium‐catalyzed intermolecular asymmetric allylic amination reaction with 2‐hydroxypyridines has been developed, thus providing a highly efficient synthesis of enantioenriched N‐substituted 2‐pyridone derivatives from readily available starting materials. This protocol features good tolerance functional groups in both the carbonates and 2‐hydroxypyridines, thereby delivering multifunctionalized heterocyclic products up to 98 % yield 99 ee .

An efficient synthesis of spiroindolenine derivatives via a ruthenium-catalyzed intramolecular allylic dearomatization reaction has been developed. This method features wide substrate scope, mild conditions, and an operationally simple procedure.

The intermolecular dearomatization reaction of indoles with allylic alcohols has been realized by a Ru-complex in the presence catalytic amount TsOH·H2O. proceeded mainly via cascade sequence including dearomatization/cyclization/allylic amination reaction, enabling introduction an substituent at both C-3 and N-1 positions indoles.

Highly regio- and enantioselective rhodium-catalyzed allylic alkylation of 1,3-diketones with racemic secondary alcohols is reported. In the presence a Rh-catalyst derived from Carreira (P, olefin)-ligand TFA as an additive, chiral branched α-allylated could be obtained in good to excellent yields, enantioselectivity (b/l > 19/1, 86–98% ee). The direct utilization allyl electrophiles represents improvement viewpoint atom economy. Both aryl- aliphatic-substituted are suitable substrates...

Visible-light-induced dearomatization reaction via energy-transfer mechanism is an emerging strategy for the synthesis of highly strained polycyclic molecules. Transient, high-energy diradical species are typically involved in this type as key intermediates. Herein, we report visible-light-induced divergent indole-tethered O-methyl oximes, which reactions open-shelled singlet intermediates toward competitive [2 + 2] cycloaddition or 1,5-hydrogen atom transfer can be achieved with exclusive...

Open AccessCCS ChemistryRESEARCH ARTICLE1 Jan 2021Visible-Light-Mediated Synthesis of Cyclobutene-Fused Indolizidines and Related Structural Analogs Min Zhu, Xu-Lun Huang, Hao Xu, Xiao Zhang, Chao Zheng Shu-Li You Zhu State Key Laboratory Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute Organic University Chinese Academy Sciences, 200032 School Physical Science Technology, ShanghaiTech University, 201210 , Huang Xu Zhang *Corresponding author(s):...

An intermolecular hydroalkylative dearomatization of naphthalenes with commercially available α-amino acids is achieved via visible-light photoredox catalysis. With an organic photocatalyst, a series multi-substituted 1,2-dihydronaphthalenes are obtained in good-to-excellent yields. Intriguingly, by tuning the substituents at C2 position naphthalenes, formal dearomative [3+2] cycloadditions occur exclusively dearomatization-cyclization sequence. This overall redox-neutral method features...

We report here a novel C(sp3)–P bonds formation via copper-catalyzed reductive coupling of N-tosylhydrazones with H-phosphorus oxides. A variety aliphatic and aromatic substrates bearing electron-rich electron-deficient substituents affords phosphine oxide derivatives moderate to good yields. This work suggests new transformation aldehydes/ketones organophosphorus compounds.