Stereospecific Stille-coupling reaction of (Z)-1,2- bis(trimethylstannyl)ethenes with hypervalent iodonium salts

Tetrahedron Letters

Volumn 40, Issue 18, 1999, Pages 3573-3576

  Kang, Suk Ku ^a   Lee, Yong Tack ^a   Lee, Sang Ho ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

Hypervalent element; Palladium and compounds; Regioselection; Stereoselection; Stille coupling; Tin and compounds

Indexed keywords

ALKENE; DIPHENYLIODONIUM SALT; ETHYLENE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033617127     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00575-4     Document Type: Article

References (15)

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2. [1] For reviews, see: (a) Stille JK. Angew. Chem. Int. Ed. Engl. 1986;25:508-524. (b) Mitchell TN. Synthesis 1992;803-815. (c) Farina, V. In Comprehensive Organometallic Chemistry II; Abel EW, Stone FGA, Wilkinson G, Ed. Pergamon Press: New York, 1995; Vol. 12, Chapter 3,4; pp 200-221. (d) Farina V. Pure Appl. Chem. 1996;68:73-78.
3. [1] For reviews, see: (a) Stille JK. Angew. Chem. Int. Ed. Engl. 1986;25:508-524. (b) Mitchell TN. Synthesis 1992;803-815. (c) Farina, V. In Comprehensive Organometallic Chemistry II; Abel EW, Stone FGA, Wilkinson G, Ed. Pergamon Press: New York, 1995; Vol. 12, Chapter 3,4; pp 200-221. (d) Farina V. Pure Appl. Chem. 1996;68:73-78.
4. [1] For reviews, see: (a) Stille JK. Angew. Chem. Int. Ed. Engl. 1986;25:508-524. (b) Mitchell TN. Synthesis 1992;803-815. (c) Farina, V. In Comprehensive Organometallic Chemistry II; Abel EW, Stone FGA, Wilkinson G, Ed. Pergamon Press: New York, 1995; Vol. 12, Chapter 3,4; pp 200-221. (d) Farina V. Pure Appl. Chem. 1996;68:73-78.
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7. [3] (Z)-1,2-bis(stannyl)ethenes: (a) Shair MD, Yoon T, Danishefsky, SJ. J. Org. Chem. 1994:59:3755-3757. (b) Mitchell TN, Kwetkat K, Rutschow D, Schnelder U. Tetrahedron 1989:45:969-978. (E)-1,2-bis(stannyl)ethenes: (c) Catellani M, Luzzati S, Musco A, Speroni F. Synthetic Metals 1994:62:223-228. (d) Djuric SW, Haack RA, Yu SS. J. Chem. Soc. Perkin Trans. 1 1989:2133-2134. (e) Haack RA, Penning TD, Djuric SW, Dziuba JA. Tetrahedron Lett.1988:29:2783-2786.
8. [3] (Z)-1,2-bis(stannyl)ethenes: (a) Shair MD, Yoon T, Danishefsky, SJ. J. Org. Chem. 1994:59:3755-3757. (b) Mitchell TN, Kwetkat K, Rutschow D, Schnelder U. Tetrahedron 1989:45:969-978. (E)-1,2-bis(stannyl)ethenes: (c) Catellani M, Luzzati S, Musco A, Speroni F. Synthetic Metals 1994:62:223-228. (d) Djuric SW, Haack RA, Yu SS. J. Chem. Soc. Perkin Trans. 1 1989:2133-2134. (e) Haack RA, Penning TD, Djuric SW, Dziuba JA. Tetrahedron Lett.1988:29:2783-2786.
9. [3] (Z)-1,2-bis(stannyl)ethenes: (a) Shair MD, Yoon T, Danishefsky, SJ. J. Org. Chem. 1994:59:3755-3757. (b) Mitchell TN, Kwetkat K, Rutschow D, Schnelder U. Tetrahedron 1989:45:969-978. (E)-1,2-bis(stannyl)ethenes: (c) Catellani M, Luzzati S, Musco A, Speroni F. Synthetic Metals 1994:62:223-228. (d) Djuric SW, Haack RA, Yu SS. J. Chem. Soc. Perkin Trans. 1 1989:2133-2134. (e) Haack RA, Penning TD, Djuric SW, Dziuba JA. Tetrahedron Lett.1988:29:2783-2786.
10. [3] (Z)-1,2-bis(stannyl)ethenes: (a) Shair MD, Yoon T, Danishefsky, SJ. J. Org. Chem. 1994:59:3755-3757. (b) Mitchell TN, Kwetkat K, Rutschow D, Schnelder U. Tetrahedron 1989:45:969-978. (E)-1,2-bis(stannyl)ethenes: (c) Catellani M, Luzzati S, Musco A, Speroni F. Synthetic Metals 1994:62:223-228. (d) Djuric SW, Haack RA, Yu SS. J. Chem. Soc. Perkin Trans. 1 1989:2133-2134. (e) Haack RA, Penning TD, Djuric SW, Dziuba JA. Tetrahedron Lett. 1988:29:2783-2786.
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15. [6] The compound 3a was treated with MeOH/AcOH (10 : 1) at room temperature to give trans-stilbene in 80% yield.