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van Leeuwen, P. W. N. M.: 2014 Science of Synthesis, 2013/8: C-1 Building Blocks in Organic Synthesis 2 DOI: 10.1055/sos-SD-213-00191
C-1 Building Blocks in Organic Synthesis 2

2.5.7 Formylation and the Vilsmeier Reagent

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Book

Editor: van Leeuwen, P. W. N. M.

Authors: Ballini, R.; Belderrain, T. R.; Bruneau, C.; Cokoja, M.; Dong, D.; Fischmeister, C.; Grushin, V. V.; Hu, J.; Ibrahim, H.; Iwasawa, N.; Kaposi, M.; Kühn, F. E.; Lishchynskyi, A.; Merino, P.; Molander, G. A.; Müller, C.; MuÇoz-Molina, J. M.; Neumann, H.; Ni, C.; Nicasio, M. C.; Novák, P.; Nozaki, K.; Ouali, A.; Petrini, M.; Rutjes, F. P. J. T.; Ryu, D.; Schoonen, L.; Schranck, J.; Taillefer, M.; Takahashi, K.; Takaya, J.; te Grotenhuis, C.; Witt, J.; Zhang, N.

Title: C-1 Building Blocks in Organic Synthesis 2

Subtitle: Alkenations, Cross Couplings, Insertions, Substitutions, and Halomethylations

Print ISBN: 9783131751218; Online ISBN: 9783132064515; Book DOI: 10.1055/b-003-125817

1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: C-1 Building Blocks in Organic Synthesis

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

Formylation, allowing the introduction of a formyl group to an organic molecule, is a useful reaction in organic synthesis. The obtained formyl group can be readily reduced to afford alcohols or oxidized to give acids. Moreover, formylation plays a key role in biological and pharmaceutical fields. This chapter covers formylating reagents that are capable of efficiently introducing a formyl group to various organic molecules. Due to the versatility, ease of operation, and tolerance of many functional groups, the Vilsmeier reaction for the formylation of organic compounds is the main focus of this chapter.

Key words

formylation - magnesium methoxide - paraformaldehyde - hexamethylenetetramine - acid - carbon monoxide - N-methylaniline - transition metal - Vilsmeier–Haack reaction - Vilsmeier reagent - halomethyleniminium salts - phosphoryl chloride - dimethylformamide
 
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