Palladium-catalyzed dimerization-carbostannylation of alkynes: Synthesis of highly conjugated alkenylstannanes

Journal of the American Chemical Society

Volumn 121, Issue 17, 1999, Pages 4290-4291

  Shirakawa, Eiji ^a   Yoshida, Hiroto ^b   Nakao, Yoshiaki ^b   Hiyama, Tamejiro ^b  

^a JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; IMINE; PALLADIUM;

ARTICLE; CHEMICAL STRUCTURE; DIMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033526336     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990008c     Document Type: Article

References (15)

1. For a review on carbometalation, see: Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 4.4; pp 865-911; Carbocupration, see: Normant, J. F.; Alexakis, A. Synthesis 1981, 841-870; Zirconium-catalyzed carboalumination, see: Negishi, E.; Takahashi, T. Synthesis 1988, 1-19; Nickel-catalyzed carbozincation, see: Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93-95.
2. For a review on carbometalation, see: Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 4.4; pp 865-911; Carbocupration, see: Normant, J. F.; Alexakis, A. Synthesis 1981, 841-870; Zirconium-catalyzed carboalumination, see: Negishi, E.; Takahashi, T. Synthesis 1988, 1-19; Nickel-catalyzed carbozincation, see: Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93-95.
3. For a review on carbometalation, see: Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 4.4; pp 865-911; Carbocupration, see: Normant, J. F.; Alexakis, A. Synthesis 1981, 841-870; Zirconium-catalyzed carboalumination, see: Negishi, E.; Takahashi, T. Synthesis 1988, 1-19; Nickel-catalyzed carbozincation, see: Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93-95.
4. For a review on carbometalation, see: Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 4.4; pp 865-911; Carbocupration, see: Normant, J. F.; Alexakis, A. Synthesis 1981, 841-870; Zirconium-catalyzed carboalumination, see: Negishi, E.; Takahashi, T. Synthesis 1988, 1-19; Nickel-catalyzed carbozincation, see: Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93-95.
5. (a) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987.
6. (b) Paquette, L. A. Org. React. 1997, 50, 1-652.
7. Shirakawa, E.; Yoshida, H.; Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975-2976.
8. Configuration of Sa was determined by the coupling constants in NMR shown below. For the coupling constants between an allylic carbon and an olefinic proton in an enyne, see: Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy, 3rd ed.; VCH: New York, 1987; Chapter 3.2. For those between a tin and an olefinic proton in an alkenylstannane, see: Leusink, A. J.; Budding, H. A.; Marsman, J. W. J. Organomet. Chem. 1967, 9, 285-294. (equation presented)
9. Configuration of Sa was determined by the coupling constants in NMR shown below. For the coupling constants between an allylic carbon and an olefinic proton in an enyne, see: Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy, 3rd ed.; VCH: New York, 1987; Chapter 3.2. For those between a tin and an olefinic proton in an alkenylstannane, see: Leusink, A. J.; Budding, H. A.; Marsman, J. W. J. Organomet. Chem. 1967, 9, 285-294. (equation presented)
10. Configuration of 5b-f was determined in a mannaer similar to 5a. Minor products 6d-f were confirmed to be regioisomers by the coupling constants between olefinic protons and those between a tin and an olefinic proton. For example, the data of 6d are shown below. (equation presented)
11. No isomer was obtained in the reaction of 3b. Syn-addition in the use of 3a led us to the conclusion that carbostannylation products 5g-m are also syn-adducts.
12. (a) van Beizen, R.; Hoffmann, H.; Elsevier, C. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1743-1745.
13. (b) van Beizen, R.; Klein, R. A.; Kooijman, H.; Veldman, N.; Spek, A. L.; Elsevier, C. J. Organometallics 1998, 17, 1812-1825.
14. (a) Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359-5364.
15. (b) Bellina, F.; Carpita, A.; Santis, M. D.; Rossi, R. Tetrahedron 1994, 50, 12029-12046.