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Synthesis 2001(13): 1993-2002
DOI: 10.1055/s-2001-17712
DOI: 10.1055/s-2001-17712
PAPER
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of 2,2"-Biscarbazoles by Reductive Biaryl Coupling [1]
Further Information
Received
11 June 2001
Publication Date:
11 August 2004 (online)
Publication History
Publication Date:
11 August 2004 (online)
Abstract
The first reductive biaryl coupling of carbazoles is presented, along with the synthesis of the appropriately halogenated coupling substrates. A completely regioselective halogenation of carbazoles was achieved applying the DoM (Directed ortho-Metalation) strategy with different combinations of directing groups. In the course of the evaluation of a suitable method for benzylic oxidations of carbazolic alcohols, a new protocol using the hypervalent iodine reagent BTIB was established.
Key words
biscarbazole - directed ortho-metalation - reductive biaryl coupling - Ullmann reaction - hypervalent iodine
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References
Some details of the synthesis of 2-halogenated carbazoles have already been part of a preliminary communication: see reference 3.
22LiAlH4 reduction led to complete reduction to give a 3-methyl group, see reference 17.