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Tuesday, 28 October 2014

A Flow Process for the Multi-Step Synthesis of the Alkaloid Natural Product Oxomaritidine: A New Paradigm for Molecular Assembly

 A Flow Process for the Multi-Step Synthesis of the Alkaloid Natural Product Oxomaritidine: A New Paradigm for Molecular Assembly 
I.R. Baxendale, J. Deeley, C.M. Griffiths-Jones, S.V. Ley, S. Saaby and G. Tranmer, J. Chem. Soc., Chem. Commun. 2006, 2566-2568.

A flow process for the multi-step synthesis of the alkaloid natural product (±)-oxomaritidine is described, mediated through the use of microfluidic pumping systems that progress material through various packed columns containing immobilized reagents, catalysts, scavengers or catch and release agents; our route involves the combination of seven separate synthetic steps linked into one continuous sequence utilizing flow chemistry.

A Fully Automated Continuous Flow Synthesis of 4,5-Disbustituted Oxaxoles

A Fully Automated Continuous Flow Synthesis of 4,5-Disbustituted Oxaxoles 
M. Baumann, I.R. Baxendale, S.V. Ley, C.D. Smith and G.K. Tranmer, Org. Lett. 2006, 8, 5231-5234.

 A multipurpose mesofluidic flow reactor capable of producing gram quantities of material has been developed as an automated synthesis platform for the rapid on-demand synthesis of key building blocks and small exploratory libraries. The reactor is configured to provide the maximum flexibility for screening of reaction parameters that incorporate on-chip mixing and columns of solid supported reagents to expedite the chemical syntheses.

Friday, 17 October 2014

Versatile, High Quality and Scalable Continuous Flow Production of Metal-Organic Frameworks

Schematic representation showing the general flow reactor setup for the production of MOFs.
The precursor solutions are pumped continuously, mixed via a static-mixer (T-piece) and 
enter the coiled reactor tubes at temperature (T). A backpressure regulator (BPR) situated
after the reactor coil is used to maintain a constant liquid pressure. 
The residence time can be varied by changing the length of the reactor or pumping rates.

Figure 1: Schematic representation showing the general flow reactor
 setup for the production of MOFs.

Further deployment of Metal-Organic Frameworks in applied settings 
requires their ready preparation at scale. Expansion of typical batch
 processes can lead to unsuccessful or low quality synthesis for some 
systems. Here we report how continuous flow chemistry can be
 adapted as a versatile route to a range of MOFs, by emulating 
conditions of lab-scale batch synthesis. This delivers ready 
synthesis of three different MOFs, with surface areas that 
closely match theoretical maxima, with production rates 
of 60 g/h at extremely high space-time yields.

Friday, 26 September 2014

Synthesis of Acetal Protected Building Blocks using Flow Chemistry and Flow I.R. Methods: Preparation of Butane 2, 3- Diacetal Tartrates

C.F. Carter, I.R. Baxendale, M. O’Brien, J.B.J. Pavey, S.V. Ley, Org. Biomol. Chem2009, 7, 4594.

Corresponding authors
Department of Chemistry, Innovative Technology Centre, University of Cambridge, Lensfield Road, Cambridge, UK
E-mail: svl1000@cam.ac.uk
AstraZeneca, Bakewell Road, Loughborough, Leics, UK

The syntheses of butane-2,3-diacetal protected tartrate derivatives are described using continuous flow processing techniques with in-line purification and I.R. analytical protocol

Tuesday, 23 September 2014

Acceptorless dehydrogenative coupling of primary alcohols to esters by heterogeneous Pt catalysts

Catal. Sci. Technol., 2014, 4,3631-3635
DOI: 10.1039/C4CY00979G, Communication
Sondomoyee Konika Moromi, S. M. A. Hakim Siddiki, Md. Ayub Ali, Kenichi Kon, Ken-ichi Shimizu
Pt/SnO2 is presented as the first example of a reusable heterogeneous catalyst for acceptorless dehydrogenative coupling of primary alcohols to esters under additive-free and solvent-free conditions.

 Supported platinum catalysts have been studied for the acceptor-free dehydrogenative 
coupling of primary alcohols to esters in the liquid phase under solvent-free conditions in N2 at 180 °C. 
The activity depends on the support material, and Pt-loaded SnO2 (Pt/SnO2) gives the highest activity. Pt/SnO2 shows higher activity than various transition metals
 (Ir, Re, Ru, Rh, Pd, Ag, Co, Ni, Cu) loaded on SnO2. The Pt/SnO2  
catalyst (1 mol%) selectively converted various primary alcohols to their corresponding esters in moderate to 
high isolated yield (53–91%). This is the first example of reusable heterogeneous catalysts for the acceptor-free dehydrogenative coupling of primary alcohols to esters 
under additive-free and solvent-free conditions. Mechanistic and infrared
 (IR) studies are also shown to discuss the reaction pathway and a possible role of the SnO2 support as Lewis acid sites that activate carbonyl groups of adsorbed aldehyde intermediates.

Acceptorless dehydrogenative coupling of primary alcohols to esters by heterogeneous Pt catalysts

Corresponding authors
Catalysis Research Center, Hokkaido University, N-21, W-10, Sapporo 001-0021, Japan 
E-mail: kshimizu@cat.hokudai.ac.jp;
Fax: +81 11 706 9163
Elements Strategy Initiative for Catalysts and Batteries, Kyoto University, Katsura, Kyoto 615-8520, Japan
Catal. Sci. Technol., 2014,4, 3631-3635

DOI: 10.1039/C4CY00979G


Monday, 22 September 2014

A Catalyst That Multitasks To Make Complex Molecules Organic Synthesis: Method leads to complex, biologically relevant molecules on gram scale

A copper catalyst guides this multicomponent reaction. 
A new synthetic strategy that relies on a multitasking copper catalyst allows chemists to construct useful molecules faster and with higher yield. Experts say it promises to fast-track complicated syntheses.
Fewer steps in a chemical synthesis often translate to a better yield of the final product. Chemists therefore prize so-called multicomponent reactions that orchestrate the assembly of multiple building blocks into a complex structure in a single stroke.
Boston College chemists Amir H. Hoveyda, Fanke Meng, and Kevin P. McGrath demonstrate their virtuosity in this regard by using an inexpensive copper catalyst that puts together complex molecules from an allene, a diboron reagent, and an allylic phosphate. The resulting products contain a stereogenic carbon center, a monosubstituted alkene, and a tough-to-synthesize Z-trisubstituted alkenylboron (Nature 2014, DOI: 10.1038/nature13735).

Sunday, 21 September 2014

Metal-free coupling of saturated heterocyclic sulfonylhydrazones with boronic acids


 Department of Chemistry, University of Cambridge, Cambridge, CB2 1EW, U.K.
 Neusentis Chemistry, Pfizer Worldwide Research and Development, The Portway Building, Granta Park, Cambridge, CB21 6GS, U.K.
J. Org. Chem.201479 (1), pp 328–338
DOI: 10.1021/jo402526z

The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones with aryl and heteroaromatic boronic acids. This procedure enables a simple, two-step synthesis of a range of functionalized sp2–sp3 linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent ketones.