Carbon Isotope exchange in late stage One-Pot Carbonylative Sonogashira reactions

Abstract

Carbonylative cross coupling reactions are of high interest in many organic chemistry syntheses, because they cover numerous organic transformations. A huge number of publications have been done in the last years with regard to C-C cross coupling reactions, but not many of them are related to one- pot late stage functionalization. In this thesis a novel methodology for one-pot carbonylative Sonogashira coupling reaction has been established. In this process aryl iodides are used as starting materials and N-formyl saccharin is employed as CO source, in order to avoid CO gas directly. Carbon isotope exchange has also been studied. For that labeled CO source is used; 13C N-Formyl saccharin. The introduction of 14C in this procedure could in one future be used for different analysis of regulative administrations as part of drug discovery and development processes.

Akoplamendu gurutzatu karbonilatiboko erreakzioak oso interesgarriak dira kimika organikoaren sintesi askotan, eraldaketa organiko ugari hartzen dituztelako. Azken urteotan, C-C akoplamendu gurutzatuaren erreakzioei buruzko argitalpen ugari egin dira, baina ez dira asko pote batean eta fase berantiar baten funtzionalizazioari buruzkoak. Tesi honetan Sonogashira karbonilazio akoplamenduerreakziorako metodologia berritzaile bat ezarri da, erreakzioa pote batean eginez. Prozesu honetan, ioduro ariloak erabiltzen dira abiapuntuko material bezala, eta N-formilsakarina erabiltzen da karbono monoxidoaren iturri bezala, zuzenean CO gasa erabili beharrean. Karbono-isotopo trukea ere aztertu da. Horretarako 13C N-formilsakarina etiketa-iturria erabili da. 14C etorkizunean prozedura honetan ere erabil liteke administrazio arautzaileen analisi desberdinetarako, sendagaiak aurkitzeko eta garatzeko prozesuen zati gisa.