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DOI: 10.1055/s-0035-1562538
Selective Synthesis, Characterization of Isomerically Pure Arylated Benzo[1,2-b:6,5-b′]dithiophenes by Regioselective Suzuki–Miyaura Reaction and Evaluation of the Catalytic Properties of Nickel versus Palladium Complexes
Publication History
Received: 09 June 2016
Accepted after revision: 21 July 2016
Publication Date:
01 September 2016 (online)
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Abstract
Selective synthesis of isomerically pure, angular-shaped benzo[1,2-b:6,5-b′]dithiophenes and various aryl-substituted analogues via the regioselective Suzuki–Miyaura cross-coupling reaction is described. The structural assignments of symmetrical and unsymmetrical derivatives of benzodithiophenes and coumarin-type polyheterocycles are based on X-ray crystallography and spectroscopic studies. A comparative study of nickel versus palladium complexes demonstrated that the nickel complex NiCl2(dppe) is more effective in terms of reactivity and yields than palladium catalysis in the Suzuki–Miyaura cross-coupling of hindered 3,6-dichlorobenzo[1,2-b:6,5-b′]dithiophenes with arylboronic acids.
Key words
isomeric purity - symmetry - spectroscopy - regioselectivity - benzodithiophenes - Suzuki–Miyaura reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562538.
- Supporting Information
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