Synthesis of 2,2 '-biscarbazoles by reductive biaryl coupling

Authors
Tasler, S Endress, H Bringmann, G
Citation
S. Tasler et al., Synthesis of 2,2 '-biscarbazoles by reductive biaryl coupling, SYNTHESIS-S, (13), 2001, pp. 1993-2002
Citations number
82
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
13
Year of publication
2001
Pages
1993 - 2002
Database
ISI
SICI code
0039-7881(200110):13<1993:SO2'BR>2.0.ZU;2-N
Abstract
The first reductive biaryl coupling of carbazoles is presented, along with the synthesis of the appropriately halogenated coupling substrates. A compl etely regioselective halogenation of carbazoles was achieved applying the D oM (Directed ortho-Metalation) strategy with different combinations of dire cting groups. In the course of the evaluation of a suitable method for benz ylic oxidations of carbazolic alcohols, a new protocol using the hypervalen t iodine reagent BTIB was established.