Daniel Moock’s research while affiliated with Monash University (Australia) and other places

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Publications (1)


N-Heterocyclic Carbene Catalyzed Transformylation
  • Article

August 2017

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42 Reads

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2 Citations

Synthesis

Jared E. M. Fernando

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Alison Levens

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Daniel Moock

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David W. Lupton 

The N-heterocyclic carbene (NHC) catalyzed transformylation has been developed for the conversion of 1°, 2°, and 3° alcohols to the corresponding formates. The reaction employs low catalyst loadings and methyl formate as the formyl transfer reagent. The scope of the reaction is broad with 23 examples reported with good yields (59–96%). The reaction is insensitive to common nitrogen and oxygen protecting groups and can be achieved in the presence of a number of heterocycles.

Citations (1)


... Our approach is essentially the first example for the synthesis of formate esters employing a formaldehyde-alcohol oxidative coupling. Generally, formate esters can be prepared by the acid-catalyzed [23] or N-heterocyclic carbene-promoted [24] transesterification of The Au-NP-catalyzed aerobic oxidation of hemiacetals has been well documented in the literature, as a protocol to prepare esters or lactones [18][19][20][21][22]. Yet for acyclic esters, one of the reactants has to be used in large excess (e.g., the reaction of benzaldehyde in methanol as a solvent to form methyl benzoate). Our approach is essentially the first example for the synthesis of formate esters employing a formaldehyde-alcohol oxidative coupling. ...

Reference:

Synthesis of Formate Esters and Formamides Using an Au/TiO₂-Catalyzed Aerobic Oxidative Coupling of Paraformaldehyde
N-Heterocyclic Carbene Catalyzed Transformylation
  • Citing Article
  • August 2017

Synthesis