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Literature DB >> 19035612

A phosphine-mediated conversion of azides into diazo compounds.

Abstract

N2 the mild: Diazo compounds are extremely versatile intermediates for synthetic organic chemistry, but their synthesis can be challenging in the presence of delicate functional groups. The Staudinger ligation has inspired a mild method for the conversion of a broad range of azides into their diazo compound derivatives through an acyl triazene intermediate.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2009 PMID： 19035612 PMCID： PMC3128508 DOI： 10.1002/anie.200804689

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

21 in total

1. Cascade Processes of Metallo Carbenoids.

Authors: Albert Padwa; M. David Weingarten
Journal: Chem Rev Date: 1996-02-01 Impact factor: 60.622

2. Isolation and characterization of azaserine.

Authors: Q R BARTZ; C C ELDER; R P FROHARDT; S A FUSARI; T H HASKELL; D W JOHANNESSEN; A RYDER
Journal: Nature Date: 1954-01-09 Impact factor: 49.962

Review 3. The Staudinger ligation-a gift to chemical biology.

Authors: Maja Köhn; Rolf Breinbauer
Journal: Angew Chem Int Ed Engl Date: 2004-06-14 Impact factor: 15.336

4. Mechanistic investigation of the staudinger ligation.

Authors: Fiona L Lin; Helen M Hoyt; Herman van Halbeek; Robert G Bergman; Carolyn R Bertozzi
Journal: J Am Chem Soc Date: 2005-03-02 Impact factor: 15.419

5. A new antibiotic, kinamycin.

Authors: S Itŏ; T Matsuya; S Omura; M Otani; A Nakagawa
Journal: J Antibiot (Tokyo) Date: 1970-06 Impact factor: 2.649

6. Cell surface engineering by a modified Staudinger reaction.

Authors: E Saxon; C R Bertozzi
Journal: Science Date: 2000-03-17 Impact factor: 47.728

7. An investigation of Staudinger reactions involving cis-1,3,5-triazidocyclohexane and tri(alkylamino)phosphines.

Authors: Xiaodong Liu; Natesan Thirupathi; Ilia A Guzei; John G Verkade
Journal: Inorg Chem Date: 2004-11-15 Impact factor: 5.165

8. Water-soluble phosphinothiols for traceless staudinger ligation and integration with expressed protein ligation.

Authors: Annie Tam; Matthew B Soellner; Ronald T Raines
Journal: J Am Chem Soc Date: 2007-08-22 Impact factor: 15.419

9. Selective tryptophan modification with rhodium carbenoids in aqueous solution.

Authors: John M Antos; Matthew B Francis
Journal: J Am Chem Soc Date: 2004-08-25 Impact factor: 15.419

10. First synthesis of 2'-deoxyfluoropuromycin analogues: experimental insight into the mechanism of the Staudinger reaction.

Authors: Adib Charafeddine; Wissam Dayoub; Hubert Chapuis; Peter Strazewski
Journal: Chemistry Date: 2007 Impact factor: 5.236

17 in total

A phosphine-mediated conversion of azides into diazo compounds.

1. Cascade Processes of Metallo Carbenoids.

2. Isolation and characterization of azaserine.

Review 3. The Staudinger ligation-a gift to chemical biology.

4. Mechanistic investigation of the staudinger ligation.

5. A new antibiotic, kinamycin.

6. Cell surface engineering by a modified Staudinger reaction.

7. An investigation of Staudinger reactions involving cis-1,3,5-triazidocyclohexane and tri(alkylamino)phosphines.

8. Water-soluble phosphinothiols for traceless staudinger ligation and integration with expressed protein ligation.

9. Selective tryptophan modification with rhodium carbenoids in aqueous solution.

10. First synthesis of 2'-deoxyfluoropuromycin analogues: experimental insight into the mechanism of the Staudinger reaction.

1. Optimized diazo scaffold for protein esterification.

Review 2. Diazo Compounds: Versatile Tools for Chemical Biology.

3. Advances in Bioconjugation.

4. Conversion of azides into diazo compounds in water.

5. A traceless Staudinger reagent to deliver diazirines.

6. Rapid cycloaddition of a diazo group with an unstrained dipolarophile.

7. Diazo Compounds as Highly Tunable Reactants in 1,3-Dipolar Cycloaddition Reactions with Cycloalkynes().

8. Fluorogenic Strain-Promoted Alkyne-Diazo Cycloadditions.

9. Discovery of a Diazo-Forming Enzyme in Cremeomycin Biosynthesis.

10. Cytosolic Delivery of Proteins by Bioreversible Esterification.