A Facile Synthesis of Thioalkyl- and Di(thioalkyl)-Substituted Bipyridines

Abstract

A convenient three-step synthesis has been developed to prepare a series of homologous 4,4′-di(ω-thioalkyl)-2,2′-bipyridines from 4,4′-dimethylbipyridine. The smallest member of the series, 4,4′-di(thiomethyl)-2,2′-bipyridine, has been synthesized by a slightly different route from 4,4′-bis(trimethylsilylmethyl)-2,2′-bipyridine; the monothiomethyl analogue has been obtained from the corresponding mono(trimethylsilylmethyl)bipyridine. Additionally, the chlororheniumtricarbonyl complex of each of the new thiol-substituted ligands has been prepared.

Key words

bipyridine - thiol - ligands - iodination - alkylation

References

• 1a Fujihara M. Rubinstein J. Rusling JF. In Encyclopedia of Electrochemistry   Vol. 10:  Bard AJ. Stratmann M. Wiley-VCH; Weinheim: 2007. 
• 1b Fan J. Gao Y. J. Exp. NanoSci.  2006,  1:  457 
• 2 For lead references, see: Nishihara H. Kanaizuka K. Nishimori Y. Yamanoi Y. Coord. Chem. Rev.  2007,  251:  2674 
• For examples, see:
• 3a Wang J. Li J. Baca AJ. Hu J. Zhou F. Yan W. Pang DW. Anal. Chem.  2003,  75:  3941 
• 3b Rieter WJ. Taylor KML. Lin W. J. Am. Chem. Soc.  2007,  129:  9852 
• 3c Vega RA. Maspoch D. Shen CK.-F. Kakkassery JJ. Chen BJ. Lamb RA. Mirkin CA. ChemBioChem  2006,  7:  1653 
• For lead references, see:
• 4a Huang J. Stockwell D. Huang Z. Mohler DL. Lian T. J. Am. Chem. Soc.  2008,  130:  5632 
• 4b Sykora M. Petruska MA. Alstrum-Acevedo J. Bezel I. Meyer TJ. Klimov VI. J. Am. Chem. Soc.  2006,  128:  9984 
• For recent reviews, see:
• 5a Murphy CJ. Gole AM. Hunyadi SE. Stone JW. Sisco PN. Alkilany A. Kinard BE. Hankins P. Chem. Commun.  2008,  544 
• 5b Daniel M.-C. Astruc D. Chem. Rev.  2004,  104:  293 
• For selected recent examples, see:
• 6a Jebb M. Sudeep PK. Pramod P. Thomas KG. Kamat PV. J. Phys. Chem. B  2007,  111:  6839 
• 6b Bertoncello P. Kefalas ET. Pikramenou Z. Unwin PR. Forster RJ. J. Phys. Chem. B  2006,  110:  10063 
• 6c Terasaki N. Akiyama T. Yamada S. Langmuir  2002,  18:  8666 
• 7 Garelli N. Vierling P. J. Org. Chem.  1992,  57:  3046 
• 8 Hu J. Fox MA. J. Org. Chem.  1999,  64:  4959 
• 9 Prior to this work, 2b had been prepared, see: Sassoon RE. Gershuni S. Rabani J. J. Phys. Chem.  1992,  96:  4692 
• 10 Gould S. Strouse GF. Meyer TJ. Sullivan BP. Inorg. Chem.  1991,  30:  2942 
• 11 Ward RS. Branciard D. Dignan RA. Pritchard MC. Heterocycles  2002,  56:  157 
• 12a Smith AP. Lamba JJS. Fraser CL. Org. Synth.  2002,  78:  82 
• 12b Fraser CL. Anastasi NR. Lamba JJS. J. Org. Chem.  1997,  62:  9314 
• 13 Lowry TH. Richardson KS. Mechanism and Theory in Organic Chemistry   3rd ed.:  Prentice Hall; New York: 1987. 
• 14 Zheng T.-C. Burkart M. Richardson D. Tetrahedron Lett.  1999,  40:  603 
• There are a number of examples of bipyridinerhenium tricarbonyl complexes with sulfur ligands; for lead references, see:
• 15a Hevia E. Pérez J. Riera V. Miguel D. Organometallics  2003,  22:  257 
• 15b Yam VW.-W. Pui YL. Wong KM.-C. Chem. Commun.  2000,  1751 
• 16 Fang Y.-Q. Hanan GS. Synlett  2003,  852