Recent developments in lanthanide mediated organic synthesis

By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) delta-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active delta-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.

/pdf/stereoselective-synthesis-of-delta-lactones-from-5-3go9l9hiuq.pdf

Stereoselective synthesis of delta-lactones from 5-oxoalkanals via one-pot sequential acetalization, Tishchenko reaction, and lactonization by cooperative catalysis of samarium Ion and mercaptan.

A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite®

It is still a challenge to integrate multiple dynamic covalent bonds (DCBs) into one network, so the effects of DCB multiplicity on the performance of covalent adaptable networks (CANs) are still unclear. In this contribution, based on the versatility of vanillin chemistry, we realized the construction of CANs containing different DCB multiplicities, and thus the influences of DCB multiplicity on the vitrimeric performance of the networks are fairly investigated. It turns out that, with increasing DCB multiplicity, the relaxation time of the networks can be reduced significantly because the dynamic performance of the CANs with double or triple DCBs is determined by not only the activation energy but the synergistic effect of different DCBs. A plausible method was first proposed to quantify the synergistic effect of DCB multiplicity. We envisage that the disclosed findings will provide significant insight into the optimized design of CANs with tunable dynamic performance.

Effects of dynamic covalent bond multiplicity on the performance of vitrimeric elastomers

Mo(CO)6 Mediated Selective Reduction of Azides and Nitro Compounds to Amines Under Neutral Conditions

Cleavage of S-S Bond by Sm/cat. CoCl2 or Sm/cat. CoCl2 • 6H2O System: A Novel Method for the Synthesis of Thiolesters

A FACILE REDUCTION OF AZIDES TO THE CORRESPONDING AMINES WITH Sm/NiCl2·6H2O SYSTEM

The Sm/cat. CoCl2 or Sm/cat. &Cl2 • 6H2O system promoted disulfides to react with anhydrides or acyl chlorides to afford thiolesters in good yields under mild and neutral conditions.

Cleavage of S—S Bond by Sm/cat. CoCl2 or Sm/cat. CoCl2×6H2O System: A Novel Method for the Synthesis of Thiolesters.

> Azides can be easily reduced to the corresponding amines with Sm/NiCl2·6H2O in excellent yields under mild and neutral conditions.

A Facile Reduction of Azides to the Corresponding Amines with Sm/NiCl2×6H2O System.

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Papers

Cleavage of S-S Bond by Sm/cat. CoCl2 or Sm/cat. CoCl2 • 6H2O System: A Novel Method for the Synthesis of Thiolesters

A FACILE REDUCTION OF AZIDES TO THE CORRESPONDING AMINES WITH Sm/NiCl2·6H2O SYSTEM

Cleavage of S—S Bond by Sm/cat. CoCl2 or Sm/cat. CoCl2×6H2O System: A Novel Method for the Synthesis of Thiolesters.

A Facile Reduction of Azides to the Corresponding Amines with Sm/NiCl2×6H2O System.