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Synthesis 2017; 49(15): 3505-3510
DOI: 10.1055/s-0036-1588449
DOI: 10.1055/s-0036-1588449
paper
N-Heterocyclic Carbene Catalyzed Transformylation
Further Information
Publication History
Received: 04 April 2017
Accepted after revision: 07 May 2017
Publication Date:
12 June 2017 (online)
Dedicated to Prof. Herbert Mayr in celebration of his 70th birthday.
Abstract
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588449. Included are experimental procedures, characterization of all new compounds and copies of 1H and 13C NMR spectra.
- Supporting Information
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For representative Vilsmeier–Haack strategies see:
For other in situ activation strategies see ref. 1b and:
For the use of formyl Bt 2:
For a recent synthesis of this reagent see:
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