A Research On The Reaction Of Indenyl-Phosphine Compound And Terminal Acetylene

Organic phosphorus chemistry,also known as life chemistry,originated in the life sciences and has been developed for more than 100 years.In this long history,organic phosphines,phosphine oxide compounds,and quaternary phosphonium salts are the three main characters.Their "performance" not only promotes the rapid progress of organophosphorus chemistry,but also accelerates the development of metal organic chemistry,catalytic chemistry,surface chemistry,pharmaceutical chemistry,materials chemistry,life sciences and other disciplines.On the other hand,indanone compounds are very important basic organic structural units,which can be widely found in many natural products and drug active molecules.And because these compounds have some excellent biological activity and optical properties,they can be widely used in drug development,dye processing,organic light-emitting materials production and so on.The traditional synthetic methods of indanone compounds often require harsh reaction conditions or tedious synthesis steps,and it is difficult to achieve industrial production.Therefore,it is particularly meaningful to find a more direct and simple,mild,efficient,and highly selective synthesis method.Based on this,this article researched the reaction of indenyl-phosphine compounds with terminal acetylenes and indenyl-phosphine compounds’oxidation reaction.The details are as follows:1.Based on the previous work of our group and on the basis of the classical Sonogashira coupling reaction,this article researched the acid-base control reaction of indenyl-phosphine compounds with terminal alkynes.Novel conjugated olefin phosphine oxide compounds 2a-2k and new quaternary phosphonium compounds 3a-3i,4a-4c were innovatively obtained.This article also found that quaternary phosphonium salt products can be efficiently converted to conjugated olefin phosphine oxide compounds under alkaline conditions.In addition,the optical properties and the anticancer activity of the quaternary phosphorous salt products 3a-3i,4a-4c were also studied.2.Based on the previous work of our group,this article used a cheap and readily available PCC as an oxidant to selectively oxidize the C-H bond on α-C of indenyl-phosphine compounds under mild conditions.A series of indanone phosphine oxide compounds 6a-6g were obtained simply and efficiently.Moreover,we have also found that PCC can also selectively oxidize indenyl compounds to obtain a series of aromatic aldehyde and ketone compounds 8a-8f and aromatic dione compounds 9a-9c.In addition,the above target products were all characterized by 1H NMR,13C NMR,19F NMR,31P NMR,and HRMS.At the same time,we were also fortunate to obtain the crystal structures of the target compounds 2a,3a,4c,6b,6c,6f,6f’.