Novel small-molecular analogues the green fluorescence protein (GFP) chromophore are synthesised to expand and improve this fluorophore family and to deepen the understanding of their fluorescence mechanism. The introduction of an aminophenyl substituent and the repositioning of the hydroxyl group to enable strong intramolecular hydrogen bonding, not only enhances fluorescence emission, but also results

A Cu-catalyzed oxidative cross-coupling of phenols with methylboronic acid to form aryl methyl ethers has been developed, expanding the scope of Chan-Evans-Lam alkylation. Electron-deficient phenol derivatives with a broad array of functional groups are methylated in high yield. Increased reaction temperature and catalyst loading enables the methylation of substrates incorporating pyridine and dihydroquinolone

Two kinds of optically active V-shaped molecules were synthesized from enantiopure disubstituted and tetrasubstituted [2.2]paracyclophane as chiral building blocks. The p- arylene-ethynylene-type π-electron systems in these species were stacked at an angle of 60°, and although the two molecules consisted of the same π-electron system, the orientations of these systems were different. In addition, their

As a simple and efficient system, Cu(OAc) 2 ·H 2 O and K 2 S 2 O 8 can activate H -phosphonates to produce the corresponding dialkyl phosphonyl radicals. The obtained dialkyl phosphonyl radicals react smoothly with 2-amino-1,4-naphthoquinones, affording accurate preparation of various phosphonyl-functionalized 2-amino-1,4-naphthoquinones. The developed copper-catalyzed cross-dehydrogenative phosphorylation

The chemical functionalization at C-5’ position of nucleosides has been significantly less studied compared to the C-1’, C-2’ and C-3’ sugar positions in spite of its potential important role for biological activity. We describe here the synthesis of new carbothioate nucleosides which were then engaged in a Liebeskind-Srogl reaction with various boronic acids for the preparation of diversely modified

Here is reported the synthesis and characterization of 4 new DB24C8-based ammonium-containing pseudorotaxanes, for which one of the two encircled axle’s extremities consists of a perfluorobutyl moiety. The subsequent dethreading of the DB24C8 over the perfluorobutyl extremity was studied. Although the perfluorobutyl extremity of an ammonium-containing axle did not allow threading of DB24C8, dethreading

We describe a domino synthesis of 4-alkylidene-3,4-dihydro-2 H -pyrroles from aryl-substituted homopropargyl sulfonamides and aldehydes promoted by cheap and easily handled TsOH·H 2 O. The present reactions proceed via cyclocondensation of α -sulfonamidoethyl- α , β -enone intermediates, which are formed by ring-cleavage of 3-acylpyrrolidines corresponding to aza-Prins cyclized intermediates. By controlling

In the quest for 3,3-dichloro-β-lactam building blocks, the serendipitous formation of 2,2-dichloro- N -(chloromethyl)acetamides was observed. This peculiar reactivity was investigated in detail, both experimentally and computationally by means of Density Functional Theory (DFT) calculations. 2,2-Dichloro-N-(chloromethyl)acetamides were thus shown to be formed experimentally through reaction of 2,2-dichloroacetyl

Herein, we report an operationally simple, cheap, and catalyst-free method for the transamidation of a diverse range of unactivated amides furnishing the desired products in excellent yields. This protocol is environmentally friendly and operates under extremely mild conditions without using any promoter or additives. Significantly, this strategy has been implied in the chemoselective synthesis of

Subsequent reduction and dearomatizing cyclization reactions open up an entry into the synthesis of novel N-fused polycyclic indolines. The dearomatizing cyclization as key step of the sequence proceeds well with Cu(OTf)2 or TfOH as catalyst. At elevated temperature reduction of nitro-substituted precursors with iron under acidic conditions affords a broad variety of polycyclic indolines directly in

Water is the solvent of choice in terms of greenness and sustainability. However, it can be difficult to isolate very polar products from water. Here, we discuss the use of n -butanol as a solvent to extract polar compounds from aqueous solution. n -Butanol produces high yields and can also be sourced sustainably from biomass, which makes it attractive from a climate perspective. The reason for its

In contrast to vinylsulfonates and vinylsulfones, vinylsulfonamides are unreactive in Pd-catalyzed oxidative Heck-coupling reactions with acetanilides. This limitation has been resolved by using a C-H-activation protocol based on Ru-Cu-Ag-catalysis. Overall, the Ru-Cu-Ag-catalyzed conditions turned out to be more reliable and showed better reproducibility than the Pd-catalyzed C-H-activation. The coupling

Substituted dibenzyl diselenides are synthesized with good yields 74-91%) via S N 2 nucleophilic substitution of benzylic trimethylammonium salts and diselenide dianion (Se 2- ) in situ generated from elemental selenium under basic condition. Highly enantiopure dibenzylic diselenides (95-98% ee) with reverse configurations to their enantioenriched quaternary ammonium salts are obtained, if benzylic

An asymmetric domino Michael/Michael reaction of α ,β-unsaturated aldehydes 1 and α -acetyl- β -substituted- α , β -unsaturated esters 2 catalyzed by diphenylprolinol silyl ether was developed. This is a formal carbo [4+2] cycloaddition reaction affording penta-substituted cyclohexanes having the three continuous chiral centers with excellent diastereo- and enantioselectivity.

Hydroformylation of alkenes and alkynes with syngas represents a method of choice to furnish valuable aldehydes with the 100% atom-economy from readily available building blocks. The field is dominated by Rh- and Co-catalysis; however, complexes of many other metals were also shown to be catalytically competent. Here we review the studies of hydroformylation under Pd-catalysis, starting from the seminal

As a consequence of the ever-increasing relevance of fluorinated drugs in medicinal chemistry, organofluorine chemistry has become a hot topic research area during the last decade. Asymmetric carbon–fluorine bond-forming reactions have enormously developed in recent years with considerable findings related to novel reactions and synthetic approaches. These new synthetic efforts have contributed to

In spite of the many resolution techniques available to separate enantiomers, diastereomeric resolution still remains the most widely used technique in industry. However, drawbacks of this technique are the limited yield of the desired enantiomer and the expensive enantiopure resolving agent that is required. We show here for the first time that a combination of diastereomeric resolution with Viedma

The full scope and limitations of the catalytic acylative kinetic resolution of a range of tertiary heterocyclic alcohols (81 examples, s up to > 200) is reported under operationally-simple conditions, using low loadings of a commercially-available Lewis basic isothiourea catalyst, HyperBTM (generally 1 mol%). The protocol is highly effective for the kinetic resolution of 3-substituted 3-hydroxyoxindole

Adamantyl H -phosphinate esters have been described by Leclaire, Giordano, and coworkers as "universal precursors of P -stereogenic compounds" after resolution by chiral HPLC, because these esters resist racemization during displacement with organometallics. In that work, the racemic esters were prepared from phosphorus trichloride or dichlorophosphines (RPCl 2 ). We decided to investigate alternative