Preparation of para-Terphenylylalkanethiols with Different Chain Lengths

Jan Müller; Markus Brunnbauer; Michael Schmidt; Anja Zimmermann; Andreas Terfort

doi:10.1055/s-2005-861841

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Preparation of para-Terphenylylalkanethiols with Different Chain Lengths

Jan Müller, Markus Brunnbauer, Michael Schmidt, Anja Zimmermann, Andreas Terfort*
Institut für Anorganische und Angewandte Chemie, Universität Hamburg, Martin-Luther-King Platz 6, 20146 Hamburg, Germany
Fax: +49(40)428386102; e-Mail: aterfort@xray.chemie.uni-hamburg.de;

Abstract

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Abstract

Terphenylylalkanethiols with different chain length were synthesized using palladium-catalyzed cross-coupling reactions. While the thiols with two and three methylene groups were obtained via photoaddition of thiopivalic acid to the respective alkenes, the longer terphenylylalkanethiols were synthesized by two consecutive Kumada cross-coupling reactions followed by a Mitsunobu reaction for the introduction of the sulfur functionality.

Key words

cross-coupling - Mitsunobu reaction - self-assembly - thiols - arylations

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References

1 Flink S. van Veggel FCJM. Reinhoudt DN. Adv. Mater. 2000, 12: 1315

2 Dudek SP. Sikes HD. Chidsey CED. J. Am. Chem. Soc. 2001, 123: 8033

3 Lahiri J. Ostuni E. Whitesides GM. Langmuir 1999, 15: 2055

4 Pirrung MC. Angew. Chem. Int. Ed. 2002, 41: 1276

5 Xia Y. Whitesides GM. Angew. Chem. Int. Ed. 1998, 37: 550

6 Murgin T. Choong V. Maracas G. Langmuir 2000, 16: 5371

7 Xia Y. Whitesides GM. Ann. Rev. Mater. Sci. 1998, 28: 153

8 Slomon A. Cahen D. Lindsay S. Tomfohr J. Engelkes VB. Frisbie CD. Adv. Mater. 2003, 15: 1881

9 Wang W. Lee T. Reed MA. Phys. Rev. B 2003, 68: 35416

10 Himmel HJ. Terfort A. Wöll C. J. Am. Chem. Soc. 1998, 120: 12069

11 Cologne J. Buendia J. Sabadie J. Bull. Soc. Chim. Fr. 1967, 83: 4370

12 Drefahl G. Tahlmann K. J. Prakt. Chem. 1963, 20: 56

13 Quelet R. Bull. Soc. Chim. Fr. 1929, 45: 75

14 During this work, the synthesis of 11 using a somewhat different route was published: Ishida T. Mizutani W. Choi N. Akiba U. Fujihira M. Tokumoto H. J. Phys. Chem. B 2000, 104: 1680

15 Belmar J. Téllez J. Baeza J. Freer J. Z. Naturforsch., B: Chem. Sci. 2000, 55: 583

16 Volante RP. Tetrahedron Lett. 1981, 22: 3119

17 Mitsunobu O. Synthesis 1981, 1

18 Kulkarni SU. Patil VD. Heterocycles 1982, 18: 163

19 Brandsma L. Vasilevsky SF. Verkruijsse HD. Application of Transition Metal Catalysts in Organic Synthesis Springer; Heidelberg: 1998.

20 Hayashi T. Mitsuo K. Makoto K. Tetrahedron Lett. 1979, 20: 1871

21 Nomura R. Miyazaki SI. Nakano T. Matsuda H. Chem. Ber. 1990, 123: 2081

22 Baldwin SW. Wilson JD. Aube J. J. Org. Chem. 1985, 50: 4432

23 Baldo MA. Chessa G. Marangoni G. Pitteri B. Synthesis 1987, 720