in organometallic chemistry

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Presentation transcript:

in organometallic chemistry Hot Topics en Hypes in organometallic chemistry 5/20/2019 Hot Topics and Hypes

Hot Topics Ideal conversions with (nearly) incompatible requirements: C-H activation and other "all-in-one" conversions Selective oxidations Anti-Markovnikov water addition (Co)polymerization of functionalized olefins Chiral conversions Mechanisms / models of enzymes 5/20/2019 Hot Topics and Hypes

Hypes Everything "BIO" and "NANO" Buckyballs, buckytubes Supramolecular chemistry Materials 5/20/2019 Hot Topics and Hypes

C-H activation Problems: C-H bond is least reactive bond Product is usually more reactive than starting material Þ further oxidation Product is always better donor than starting material Þ product inhibition 5/20/2019 Hot Topics and Hypes

C-H activation This will not work: 5/20/2019 Hot Topics and Hypes

C-H activation This does work: B-B bond weak B-H and B-C strong product hardly coordinating 5/20/2019 Hot Topics and Hypes

C-H activation A real example: Electrophilic attack on C-H bond (?) 5/20/2019 Hot Topics and Hypes

CH4 to CH3OH: how does industry do it? "hot pipes" 5/20/2019 Hot Topics and Hypes

CH4 to CH3OH: how does nature do it? (we think) MMO = "methane mono-oxygenase" 5/20/2019 Hot Topics and Hypes

C-H activation C-H activation for CH4 ® CH3OH via homogeneous catalysis is "useless" selective conversion van non-activated C-H bonds in larger molecules is highly desirable nature does this through "shape selectivity" with e.g. cytochrome P450 zeolites sometimes work quite well 5/20/2019 Hot Topics and Hypes

How can you study C-H activation? "microscopic reversibility" activation of more reactive C-H bonds e.g. aromatic Csp2-H bonds 5/20/2019 Hot Topics and Hypes

Selective oxidation Epoxidation: does not work for other olefins (allylic C-H bonds are too reactive) 5/20/2019 Hot Topics and Hypes

Selective oxidation Aldehydes / ketones: 5/20/2019 Hot Topics and Hypes

Selective oxidation Desired: Current process: hydroformylation 5/20/2019 Hot Topics and Hypes

Anti-Markovnikov water addition Desired: Current process: via hydroformylation 5/20/2019 Hot Topics and Hypes

Anti-Markovnikov water addition A possible organometallic route: 5/20/2019 Hot Topics and Hypes

(Co)polymerization of functionalized olefins Desired: Problem: 5/20/2019 Hot Topics and Hypes

(Co)polymerisation of functionalized olefins Possible solutions: Late transition metal complexes b.v. Ni/Pd Brookhart Protection of functional group Fictionalization after polymerization 5/20/2019 Hot Topics and Hypes

Chiral conversions Noyori / Knowles / Sharpless Precise tuning needed for every new reaction combinatorial catalysis? Few general principles Many "standard" chiral ligands 5/20/2019 Hot Topics and Hypes

Chiral conversions 5/20/2019 Hot Topics and Hypes