Palladium-Catalyzed C−H Homocoupling of Bromothiophene Derivatives and Synthetic Application to Well-Defined Oligothiophenes
- 29 July 2006
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (33) , 10930-10933
- https://doi.org/10.1021/ja060749v
Abstract
Synthesis of oligothiophenes of well-defined structures that possess 2−8 thiophene units is performed with a new synthetic strategy involving C−H homocoupling of bromothiophenes and cross-coupling with organostannanes. Tolerance of the carbon−bromine bond to the palladium-catalyzed C−H homocoupling results in oligothiophenes bearing C−Br bonds at the terminal thiophene rings, which allow further transformation by the catalysis of a transition-metal complex.Keywords
This publication has 21 references indexed in Scilit:
- High Carrier Mobility up to 0.1 cm2 V–1 s–1 at Ambient Temperatures in Thiophene‐Based Smectic Liquid CrystalsAdvanced Materials, 2005
- Palladium-Catalyzed C−H Homocoupling of Thiophenes: Facile Construction of Bithiophene StructureJournal of the American Chemical Society, 2004
- Building Blocks for n‐Type Organic Electronics: Regiochemically Modulated Inversion of Majority Carrier Sign in Perfluoroarene‐Modified Polythiophene SemiconductorsAngewandte Chemie International Edition in English, 2003
- Synthesis and Spectroscopic Properties of a Series of β-Blocked Long Oligothiophenes up to the 96-mer: Revaluation of Effective Conjugation LengthJournal of the American Chemical Society, 2003
- Synthesis, Optical, and Conductive Properties of Long Oligothiophenes and Their Utilization as Molecular WiresBulletin of the Chemical Society of Japan, 2001
- Oligothiophenes—Yet Longer? Synthesis, Characterization, and Scanning Tunneling Microscopy Images of Homologous, Isomerically Pure Oligo(alkylthiophene)sAngewandte Chemie International Edition in English, 1995
- Regiochemistry and Conformation of Poly(3-hexylthiophene) via the Synthesis and the Spectroscopic Characterization of the Model Configurational TriadsMacromolecules, 1994
- Selective Functionalization of 2,2'-BithiophenesHETEROCYCLES, 1991
- The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]Angewandte Chemie International Edition in English, 1986
- Spherands - ligands whose binding of cations relieves enforced electron-electron repulsionsJournal of the American Chemical Society, 1979