Synthesis and Stille Cross-Coupling
Reactions of 2-(Tributylstannyl)- and 2,5-Bis(trimethylstannyl)tellurophene

Daniel P. Sweat; Chad E. Stephens

doi:10.1055/s-0029-1216958

PAPER

Synthesis and Stille Cross-Coupling Reactions of 2-(Tributylstannyl)- and 2,5-Bis(trimethylstannyl)tellurophene

Daniel P. Sweat, Chad E. Stephens*
Department of Chemistry and Physics, Augusta State University, Augusta, GA 30904, USA
Fax: +1(706)4345597; e-Mail: cstephe7@aug.edu;

Abstract

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Abstract

Herein, we describe the synthesis and Stille cross-coupling reactions of 2-(tributylstannyl)- and 2,5-bis(trimethylstannyl)tellurophene. The reactions were most optimal when using aryl iodides as coupling partners, and a mixed catalyst system consisting of tetrakis(triphenylphosphine)palladium(0) and copper(I) iodide, together with cesium fluoride as additive, in N,N-dimethylformamide. This is the first reported synthesis and use of stannylated tellurophenes for cross-coupling reactions.

Key words

tellurophene - Stille reaction - cross-coupling - palladium - heterocyclic

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References

<A NAME="RM01409SS-1A">1a</A> Corbet J.-P. Mignani G. Chem. Rev. 2006, 106: 2651

<A NAME="RM01409SS-1B">1b</A> Li JJ. Gribble GW. Palladium in Heterocyclic Chemistry 2nd ed: Elsevier Ltd.; Amsterdam: 2007.

<A NAME="RM01409SS-2A">2a</A> Cross-Coupling Reactions: A Practical Guide Miyaura N. Springer-Verlag; Berlin / Heidelberg: 2002.

<A NAME="RM01409SS-2B">2b</A> Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4442

<A NAME="RM01409SS-3">3</A> Farina V. Krishnamurthy V. Scott WJ. Organic Reactions Vol. 50: Paquette L. Wiley; New York: 1997.

<A NAME="RM01409SS-4">4</A> Liu Y. Collar CJ. Kumar A. Stephens CE. Boykin DW. Wilson WD. J. Phys. Chem. B 2008, 112: 11809

<A NAME="RM01409SS-5A">5a</A> Rosypal AC. Werbovetz KA. Salem M. Stephens CE. Kumar A. Boykin DW. Hall JE. Tidwell RR. J. Parasitol. 2008, 94: 743

<A NAME="RM01409SS-5B">5b</A> Silva CF. Batista MM. Mota RA. de Souza EM. Stephens CE. Som P. Boykin DW. Soeiro MNC. Biochem. Pharmacol. 2007, 73: 1939

<A NAME="RM01409SS-6A">6a</A> Inoue S. Jigami T. Nozoe H. Otsubo T. Ogura F. Tetrahedron Lett. 1994, 35: 8009

<A NAME="RM01409SS-6B">6b</A> Inoue S. Jigami T. Nozoe H. Aso Y. Ogura F. Otsubo T. Heterocycles 2000, 52: 159

<A NAME="RM01409SS-7">7</A> Stephens CE. Tanious F. Kim S. Wilson WD. Schell WA. Perfect JR. Franzblau SG. Boykin DW. J. Med. Chem. 2001, 44: 1741

<A NAME="RM01409SS-8">8</A> Gronowitz S. Peters D. Heterocycles 1990, 30: 645

<A NAME="RM01409SS-9A">9a</A> Zeni G. Tetrahedron Lett. 2005, 46: 2647

<A NAME="RM01409SS-9B">9b</A> Panatieri RB. Reis JS. Borges LP. Nogueira CW. Zeni G. Synlett 2006, 3161

<A NAME="RM01409SS-10">10</A> The synthesis and coupling reaction of a related benzo[b]tellurophene-3-boronic acid derivative has been described, see: Jones RL. Dissertation Technische Universität Kaiserslautern; Germany: 2005.

<A NAME="RM01409SS-11">11</A> Seitz DE. Lee S.-H. Hanson RN. Bottaro JC. Synth. Commun. 1983, 13: 121

<A NAME="RM01409SS-12">12</A> Gonzalez JL. Stephens CE. Wenzler T. Brun R. Tanious FA. Wilson WD. Barszcz T. Werbovetz KA. Boykin DW. Eur. J. Med. Chem. 2007, 42: 552

<A NAME="RM01409SS-13">13</A> Tierney S. Heeney M. McCulloch L. Synth. Met. 2005, 148: 195

<A NAME="RM01409SS-14A">14a</A> Mee SPH. Lee V. Baldwin JE. Chem. Eur. J. 2005, 11: 3294

<A NAME="RM01409SS-14B">14b</A> Mee SPH. Lee V. Baldwin JE. Angew. Chem. Int. Ed. 2004, 43: 1132

<A NAME="RM01409SS-15">15</A> Sweat DP. Stephens CE. J. Organomet. Chem. 2008, 693: 2463

<A NAME="RM01409SS-16">16</A> Fringuelli F. Serena B. Taticchi A. J. Chem. Soc., Perkin Trans. 2 1980, 971

<A NAME="RM01409SS-17">17</A> Dabdoub MJ. Dabdoub VB. Pereira MA. Zukerman-Schpector J. J. Org. Chem. 1996, 61: 9503