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Synthesis of polycarbonyl compounds by cobalt-catalysed Diels-Alder / ozonolysis or cobalt-catalysed 1,4-hydrovinylation / ozonolysis reaction sequences

通过钴催化的 Diels-Alder/臭氧分解或钴催化的 1,4-氢乙烯基化/臭氧分解反应序列合成多羰基化合物

基本信息

批准号：
179130118
负责人：
Professor Dr. Gerhard Hilt
金额：
--
依托单位：
Institut für Chemie (IfC)
依托单位国家：
德国
项目类别：
Research Grants
财政年份：
2010
资助国家：
德国
起止时间：
2009-12-31 至 2013-12-31
项目状态：
已结题

来源：
https://gepris.dfg.de/gepris/projekt/179130118?language=en
关键词：
Synthesis polycarbonyl compounds cobalt catalysed

项目摘要

The cobalt-catalysed meta-selective Diels-Alder reaction as well as the cobalt-catalysed 1,4-hydrovinylation reaction generate 1,4-dienes with a high tolerance towards many functional groups. The 1,4-dienes obtained allow us to generate 1,3-dicarbonyl compounds by ozonolysis or other double bond cleaving reactions. Tri-, tetra- or higher polycarbonyl compounds become accessible when incorporating additional double bonds in the starting material, thus allowing a rapid increase in complexity by exceedingly short reaction sequences. An atom economic approach towards polycarbonyl derivatives is realised when symmetrical dihydroaromatic compounds are used in the ozonolysis reaction generating two identical products. The synthesis and especially the handling and characterisation of these tri-, tetra- and polycarbonyl compounds is a challenging task which we will address by complexation of the 1,3-dicarbonyl subunit with a BF2 fragment. Within these complexes the boron acts as a protecting group for the 1,3-dicarbonyl subunit, so that functional group transformations on additional uncomplexed carbonyl groups seem possible. Prototype reactions will be performed to investigate possible followup transformations towards increasingly complex products.

钴催化的间位选择性Diels-Alder反应以及钴催化的1，4-加氢乙烯基化反应产生对许多官能团具有高耐受性的1，4-二烯。得到的1，4-二烯允许我们通过臭氧分解或其他双键裂解反应生成1，3-二羰基化合物。当在起始材料中引入额外的双键时，三-、四-或更高级的多羰基化合物变得容易获得，从而允许通过极短的反应序列快速增加复杂性。当对称的二氢芳族化合物用于臭氧分解反应中产生两种相同的产物时，实现了对多羰基衍生物的原子经济方法。这些三，四和多羰基化合物的合成，特别是处理和表征是一项具有挑战性的任务，我们将解决的1，3-二羰基亚基与BF 2片段的络合。在这些配合物中，硼作为1，3-二羰基亚基的保护基，因此在额外的未络合的羰基上的官能团转化似乎是可能的。原型反应将进行调查可能的后续转化越来越复杂的产品。