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Phosphorylation of N-Silylpyrroles with Phosphorus Tribromide
✍ Scribed by Aleksandra A. Chaikovskaya; Yurii V. Dmytriv; Aleksandr M. Pinchuk; Andrei A. Tolmachev
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 109 KB
- Volume
- 19
- Category
- Article
- ISSN
- 1042-7163
- DOI
- 10.1002/hc.20416
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✦ Synopsis
Abstract
Phosphorylation of N‐trimethylsilyl‐ and N‐dimethyl‐tert‐butylsilylpyrroles with phosphorus tribromide in pyridine proceeds selectively at position 3 of the pyrrole ring. Removal of the trialkylsilyl protecting group has furnished the first representatives of N‐unsubstituted 3‐phosphorylated pyrroles. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:93–96, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20416
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## Abstract Phosphorus trichloride in a basic medium is a convenient reagent for the direct C‐phosphorylation of electron‐rich aromatic heterocycles. The compounds obtained can be used for the synthesis of various types of heteroaryl and diheteroaryl derivatives of tri‐ and pentavalent phosphorus.
## Abstract The investigation concerns the effect of a bulky substituent at the pyrrole nitrogen atom on the orientation and regioselectivity of pyrrole phosphorylation with phosphorus(III) halides. As shown, phosphorylation of N‐iso‐propylpyrrole with phosphorus tribromide or trichloride proceeds