Barton arylation
The Barton arylation is a name reaction in organic chemistry . The reaction is named after the British chemist Derek Harold Richard Barton . The Barton arylation allows the arylation of phenols , enols , azoles and amines using organobismuth compounds (e.g. an aryl-bismuth (V) compound) in an acidic or basic medium.
From 2-naphthol z. B. with a phenyl bismuth (V) compound in an acidic environment (e.g. trichloroacetic acid) of the diaryl ether 1 (Ph = phenyl). In a basic medium (with 2- tert -butyl-1,1,3,3-tetramethylguanidine), however, the β-naphthol derivative 2 is formed :
In the acidic there is an O -phenylation, in the basic one a new carbon-carbon bond is formed.
Individual evidence
- ^ University of Glasgow: Sir Derek Barton , accessed March 9, 2018.
- ↑ Alfred Hassner, Irishi Namboothiri: Organic Synthesis Based on Reaction name , Elsevier, 2012, ISBN 978-0-08-096630-4 , page 153rd
- ↑ Rudolph A. Abramovitch, Derek HR Barton, Jean-Pierre Finet: Newer Methods of Arylation. In: Tetrahedron . 44, 1988, pp. 3039-3071, doi: 10.1016 / S0040-4020 (01) 85938-X .
- ^ A b Jean-Pierre Finet: Arylation Reactions with Organobismuth Reagents. In: Chemical Reviews . 89, 1989, pp. 1487-1501, doi: 10.1021 / cr00097a005 .
- ^ Derek HR Barton: The chemistry of pentavalent organobismuth reagents: Part X. Studies on the phenylation and oxidation of phenols In: Tetrahedron . 43, 1987, pp. 323-332, doi: 10.1016 / S0040-4020 (01) 89960-9 .