Direct, organocatalytic α-sulfenylation of aldehydes and ketones

A method for direct sulfenylation of aldehydes and ketones, catalyzed by a novel pyrrolidine trifluoromethanesulfonamide organocatalyst, has been developed. This process serves as an efficient and mild approach to the preparation of α-phenylthio-ketones and -aldehydes.     

Synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction using organocatalysts

A novel and green approach for efficient and rapid synthesis of polyhydroquinoline derivatives via unsymmetric Hantzsch reaction using organocatalysts at room temperature was reported. The process is a simple, environmentally friendly, rapid, and high yielding reaction for the synthesis of polyhydroquinoline derivatives. The catalytic efficiency of various small organocatalysts such as l-proline, trans-4-hydroxy-l-proline, l-thiaproline, dl-phenylglycine, and (−)-cinchonidine was studied under aqueous, organic, and solvent free conditions.     

Starch nanoparticles as a bio-nanocatalyst in synthesis of diheteroaryl thioethers

Nanostarch is shown to be a highly efficient, eco-friendly and heterogenous organocatalyst for the synthesis of the diheteroaryl thioethers via one-pot reaction of methylcarbonyls, thiourea and iodine in DMSO. This method offers significant advantages such as available starting materials, higher purity and excellent yield of products, very easy reaction conditions and absence of any tedious purification. Furthermore, because of employing eco-friendly catalyst without using transition metal catalysts, this novel method emerges as a green-approach leading to less harmful residues. Moreover, a mechanism was proposed to rationalize the reaction and the role of starch nanoparticles was also investigated in these transformations.     

Synthesis of chiral thiourea–phosphine organocatalysts derived from l-proline

A novel class of thiourea–phosphine was prepared from l-proline as a chiral renewable resource. The original structure of the chiral framework offers an interesting potential to the construction of bifunctional organocatalysts for asymmetric transformations.     

Catalytic silylation of secondary alcohols by pyridine N-oxide derivative

The reaction of t-butyldiphenylsilyl (TBDPS) chloride with secondary alcohols was catalyzed by pyrrolidinopyridine N-oxide (PPYO) in the presence of diisopropylethylamine (DIPEA) at room temperature, giving the corresponding TBDPS ethers in high yields.     

Triphyrin catalyzed direct C–H arylation of benzene with aryl halides

Transition-metal free direct C–H arylation of benzene with aryl halides was achieved by meso-aryl-substituted [14]triphyrins(2.1.1) catalysts in an air atmosphere. Various aryl halides underwent successful direct C–H arylation of benzene to give moderate to high yields of biaryls. A radical mechanism is proposed for this triphyrin catalyzed C–H arylation reaction.     

Isoselective Ring-opening Polymerization of Racemic Lactide Catalyzed by N-heterocyclic Olefin/(Thio)urea Organocatalysts

The isoselective ring-opening polymerization of racemic lactide was achieved by combining N-heterocyclic olefin(NHO) with mono(thio)ureas or bis(thio)ureas as catalytic systems. The polymerization process shows high stereoselectivity, controllability and reactivity,delivering multi-block isotactic polylactides with high chain-end fidelity and narrow molecular weight distributions. The enhancement of catalytic performance was observed in the following order: bisthiourea(DTU) monothiourea(TU) bisurea(DU) urea(U). The highest Pm(probability of forming a meso dyad) = 0.91 was observed at-70 °C when using NHO/U1 catalytic system and the high stereoselectivity was attributed to chain-end control mechanism.     

Potassium phthalimide： An efficient and green organocatalyst for the synthesis of 4-aryl-7-（arylmethylene）-3,4,6,7-tetrahydro-1H- cyclopenta[d]pyrimidin-2（5H）-ones]thiones under solvent-free conditions

An efficient synthesis of Biginelli-type compounds using potassium phthalimide as a green, mild, and commercially available organocatalyst in a one-pot, multi-component cyclocondensation reaction of cyclopentanone, aldehydes, and urea/thiourea is reported. The present methodology is a green approach to access 4-aryl-7-（aryImethylene）-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2（5H）-ones/thiones. It offers several merits such as simple operational procedures, no use of hazardous organic solvents, and cheap and environmentally friendly solid basic catalyst.     

Highly effective and enantioselective Phospho-Aldol reaction of diphenyl phosphite with N-alkylated isatins catalyzed by quinine

Cinchona alkaloids were first successfully reported to promote enantioselective Phospho-Aldol reaction of diphenyl phosphite to a variety of N-alkylated isatin derivatives in good to excellent yields (up to 99%) and moderate to good enantioselectivities (up to 73% ee) almost in no time.     

Organocatalytic asymmetric 1,4-addition of organoboronic acids to γ-hydroxy α,β-unsaturated aldehyde: facile synthesis of chiral β-substituted γ-lactones

Catalytic asymmetric 1,4-addition of arylvinyl- and arylboronic acids to a γ-hydroxy α,β-unsaturated aldehyde, which affords β-substituted γ-lactols, has been established using a diarylprolinol silyl ether as an organocatalyst. The β-substituted γ-lactols have been obtained in good yields and with up to 91% ee, which lead to chiral β-substituted γ-lactones followed by oxidation.