Palladium-Catalyzed Cross-Coupling Reactions of 3-Tributylstannylsulfolene

Synlett

Volumn 1997, Issue 11, 1997, Pages 1273-1274

  Bew, Sean P ^a   Sweeney, J B ^a,b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002660275     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1020     Document Type: Article

References (30)

1. For pertinent references, see Oh, T.; Reilly, M.; Org. Prep. Proc. Int., 1994, 26, 129; Waldmann, H.; Synthesis, 1994, 535; Craig, D.; Chem. Soc. Rev., 1987, 16, 187, and references therein.
2. For pertinent references, see Oh, T.; Reilly, M.; Org. Prep. Proc. Int., 1994, 26, 129; Waldmann, H.; Synthesis, 1994, 535; Craig, D.; Chem. Soc. Rev., 1987, 16, 187, and references therein.
3. For pertinent references, see Oh, T.; Reilly, M.; Org. Prep. Proc. Int., 1994, 26, 129; Waldmann, H.; Synthesis, 1994, 535; Craig, D.; Chem. Soc. Rev., 1987, 16, 187, and references therein.
4. See, for instance, Nakamura, A.; Mashima, K.; J. Organomet. Chem., 1995, 500, 261.
5. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
6. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
7. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
8. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
9. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
10. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
11. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
12. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
13. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
14. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
15. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
16. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
17. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
18. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
19. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
20. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
21. For recent reports of the synthetic utility of 3-sulfolenes, see: Subramanian, T.; Meenakshi, S.; Dange, S.Y.; Bhat, S.V.; Synth. Comm., 1997, 27, 2557; Vicente, M.G.H.; Tome, A.C.; Walter, A.; Cavaleiro, J.A.S.; Tetrahedron Lett., 1997, 38, 3639; Leonard, J.; Fearnley, S.P.; Hague, A.B.; Wong, G.; Jones, M.F.; Tetrahedron Lett., 1997, 38, 3067; Suzuki, T.; Fuchii, H.; Takayama, H.; J. Chem. Soc., Perkin Trans. 1, 1996, 2699; Tso, H.H.; Chandrasekharam, M.; Tetrahedron Lett., 1996, 37, 4189; Lee, Y.S.; Ryu, E.K.; Yun, K.Y.; Kim, Y.H.; Synlett, 1996, 247; Chou, S.S.P.; Chao, M.H.; J. Chin. Chem. Soc., 1996, 43, 53; Padmakumar, R.; Subramanian, T.; Bhat, S.V.; Org. Prep. Proc. Int., 1995, 27, 463; Tso, H.H.; Yang, N.C.; Chang, Y.M.; J. Chem. Soc., Chem. Commun., 1995, 13, 1349; Kasatkin, A.N.; Prokopenko, Y.A.; Khabihov, A.M.; Tolstikov, G.A.; Russ. Chem. Bull., 1994, 43, 101; Hoffmann, R.; Mattay, J.; Banning, A.; Rodewald, U.; Moller, M.M.; J. Prakt. Chem., 1994, 336, 343; Chou, S.S.P; Lee, C.S.; Cheng, M.C.; Tai, H.P.; J. Org. Chem., 1994, 59, 2010; Ando, K.; Takayama, H.; Heterocycles, 1994, 37,1417; Ghabrial, S.S.; Phosphorus, Sulfur, Silicon And Related Elements, 1993, 84,17; Polunin, E.V.; Maloshitskaya, O.A.; Kashin, A.N.; Mendeleev Comm., 1993, 6, 254; Chou, T.S.; Tsai, C.Y.; J. Chin. Chem. Soc., 1993, 40, 581; Chou, T.S.; Chang, R.C.; Heterocycles, 1993, 36, 2839.
22. Bew, S.P.; Sweeney, J.B.; Synthesis, 1994, 698.
23. (a.) Stille, J.K.; Ang. Chem. Int. Ed. Engl., 1986, 29, 508;
24. (b.) Mitchell, T.N.; Synthesis, 1992, 803.
25. Colson, P-J.; Sedrati, M.; Franck-Neumann, M.; Tetrahedron Lett., 1989, 30, 2393.
26. Harrington, P.J.; DiFiore, K.A.; Tetrahedron Lett., 1987, 28, 495.
27. Sengupta, S.; Bhattacharyya, S.; Synth. Comm., 1996, 26, 231.
28. General procedure for coupling of aryl and alkenyl halides with (1): 3-tri-n-Butylstannyl-2,5-dihydrothiophene-1,1-dioxide (121 mg, 0.30 mmol) was dissolved in dioxan (3 mL) under a nitrogen atmosphere. To the stirred solution was added the requisite halide (0.30 mmol) and trans-benzyl(chloro)bis(triphenylphosphine) palladium(II) (26mg, 0.03mmol) or tetrakis(triphenylphosphine) palladium(0) (34 mg, 0.03 mmol). The resulting solution was heated at 80°C for twelve hours under an atmosphere of nitrogen. After this time tlc (petroleum ether/ether [8 :2]) showed that the starting materials had been consumed. The solvent was removed in vacuo and the crude product redissolved in aqueous methanol (90% v/v, 5 mL). This solution was washed with petroleum ether (3x20mL) to remove the bulk of the tin side-products. The methanolic solution was concentrated in vacuo, and the crude product purified by flash chromatography.
29. General procedure for coupling of acyl chlorides with (1): 3-tri-n-Butylstannyl-2,5-dihydrothiophene-1,1 -dioxide (54 mg, 0.13 mmol) was dissolved in chloroform (3 mL). To the stirred chloroform solution was added freshly distilled acyl chloride (0.13 mmol) and trans-benzyl(chloro)bis(triphenylphosphine)-palladium(II) (10mg, 0.01mmol). The resulting solution was heated at 80°C for twelve hours under an atmosphere of carbon monoxide. After this time tlc (petroleum ether/ether [8 :2]) showed that the starting materials had been consumed. The pure products were then obtained as described above.
30. General procedure for coupling of alkenyl triflates with (1): 3-tri-n-Butylstannyl-2,5-dihydrothiophene-1,1-dioxide (86 mg, 0.21 mmol) was dissolved in N,N-dimethylformamide (800 nitrogen atmosphere. The requisite triflate (0.21 mmol), bis[1,2-bis(diphenylphosphino)ethane]palladium(0) (9.5 mg, 0.01 mmol) and lithium chloride (45 mg, 1.06 mmol) were added via a solid-addition tube, and the resulting solution was stirred at room temperature for 48 hours. After this time tlc (petroleum ether/ether [8 :2]) showed that the starting materials had been consumed. The pure products were then obtained as described above.