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Transcript
Reporter: Sun Beiqi Supervisor: Prof. Mo Date: 3/24/2016 Outline 1. Introduction 2. CO32– -promoted C–H carboxylation 3. CO2 utilization cycle 4. CO2 as a feedstock for synthesis of FDCA 5. Carboxylates to methyl esters by reaction with CO2 Introduction 1. My last presentation is about turning CO2 to CH3OH. Now let’s think about something else. 2.Carbon dioxide has one carbon atom. How about forming CCO2 bond to synthesize potential organic compound ? 3. 2-furoic acid, from furfural, PEF , substitute of PET Introduction • Reaction Why do they use CO32- as a base to generate carboncentred nucleophile? CO32– -promoted C–H carboxylation • Researchers have shown that Cs2CO3 can deprotonate alkynyl , allylic, and activated heteroaryl C–H bonds with pKa values of up to 27 CO2 utilization cycle CO2 as a feedstock for synthesis of FDCA CO2 as a feedstock for synthesis of FDCA CO2 as a feedstock for synthesis of FDCA • Other cations • C–H carboxylation does not require Cs+, but caesium salts do typically have lower melting points CO2 as a feedstock for synthesis of FDCA • Evidence for C–H deprotonation Carboxylates to methyl esters by reaction with CO2 Carboxylates to methyl esters by reaction with CO2 Conclusion • Very simple strategy for engaging CO2 in C–C bond formation that does not require synthetic or biological catalysts. • The ability to deprotonate unactivated C–H bonds opens the possibility of using this approach to prepare numerous high-volume targets. • In particular, combining carboxylation with hydrogenation reactions may enable the synthesis of multi-carbon 谢谢大家!