Application Of Iodotrimethylsilane In Organic Synthesis

Me3SiI, a versatile reagent to promote a variety of useful synthetic transformations in the past thirty years. The thesis mainly focused on the application of Me3SiI in the organic synthesis field. This thesis is comprised of three parts.1. Benzopyran is a well-known privileged structural motif widely found in many physiologically active compounds. Me3SiI-promoted reaction of salicylic aldehydes with β-dicarbonyl compounds provided a facile way to construct4H-benzopyrans in moderate to good yields. This tandem reaction proceeds in high efficiency through nucleophilic addition, silyl enol ether formation, substitution, reduction, and intramolecular nucleophilic cyclization. The most important is that traditional methods for the reduction of carbonyl compounds to methene compounds more or less suffered from high pressure. high temperature, explosive, toxic and hazardous substances. And compared to traditional methods, the method is more safer and more efficient.2. The construction of various types of heteroannular ketals such as [2,3-b]ketals and spiroketals is a fundamental and important subject in medicinal chemistry, natural product chemistry and synthetic chemistry. Hence, in recent years, novel approaches to the synthesis of ketal have been developed. We have developed a highly versatile and uniquely enabling methodology to construct benzopyranic heteroannular ketals in one-pot from the Me3SiI-promoted reaction of salicylic aldehydes with simple ketones as well as keto-ols.3. Phosphorus compounds have emerged as a preeminent class of organic compounds which hold ubiquitous applications serving as versatile ligands for transitionmetal catalyzed reactions. On the basis of our previous work that about Me3SiI and inspired by the reaction of aldehydes with Ph2PCl. It has been a well-known reaction to give1-chloroalkylphosphine oxides at elevated temperature and the reduction of alkyl iodide with T-reagent to give reductive product with elimination of I2, the reaction of aldehydes with Ph2PI was envisioned to give1-iodoalkylphosphine oxides which were further reduced by Pb2PI to afford phosphine oxides in one pot operation. We use Ph2PI react with aldehydes.The reaction of aldehydes with Ph2PI provides an facile way to the synthesis of pentavalent phosphine compounds with moderate to good yields.