Palladium-catalyzed cross-coupling reaction of 1-aryltriazenes with aryl- and alkenyltrifluorosilanes

Advanced Synthesis and Catalysis

Volumn 346, Issue 13-15, 2004, Pages 1689-1692

  Saeki, Tomoyuki ^a   Matsunaga, Tadafumi ^a   Son, Eun Cheol ^a   Tamao, Kohei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Aryltriazene; Biaryls; Cross coupling; Palladium; Stilbene; Trifluorosilane

Indexed keywords

BORON TRIFLUORIDE; BORONIC ACID DERIVATIVE; LEWIS ACID; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILANE DERIVATIVE; STILBENE; TRIAZENE DERIVATIVE;

ACIDITY; ARTICLE; CATALYSIS; CROSS COUPLING REACTION; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 12344283745     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404212     Document Type: Article

References (17)

1. a) Metal-Catalyzed Cross-Coupling Reactions, (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998;
2. b) Cross-Coupling Reactions: A Practical Guide (Ed.: N. Miyaura), Topics in Current Chemistry, Vol. 219, Springer-Verlag, Heidelberg, 2002;
3. c) 30 Years of Cross-Coupling Reaction (Eds.: K. Tamao, E.-i. Negishi, T. Hiyama), J. Organomet. Chem. (Special Issue) 2002, 653.
4. T. Saeki, E.-C. Son, K. Tamao, Org. Lett. 2004, 6, 617.
5. D. B. Kimball, M. M. Haley, Angew. Chem. Int. Ed. 2002, 41, 3338 and references cited therein. Caution: the triazene compounds are carcinogenic; direct hand contact should be avoided.
6. Cross-coupling reactions of arenediazonium salts, one of the attractive candidates for halogen-free electrophiles, have been extensively studied: a) K. Kikukawa, K. Kono, F. Wada, T. Matsuda, J. Org. Chem. 1983, 48, 1333; b) S. Sengupta, S. Bhattacharya, J. Org. Chem. 1997, 62, 3405; c) M. B. Andrus, C. Song, Org. Lett. 2001, 3, 3761.
7. Cross-coupling reactions of arenediazonium salts, one of the attractive candidates for halogen-free electrophiles, have been extensively studied: a) K. Kikukawa, K. Kono, F. Wada, T. Matsuda, J. Org. Chem. 1983, 48, 1333; b) S. Sengupta, S. Bhattacharya, J. Org. Chem. 1997, 62, 3405; c) M. B. Andrus, C. Song, Org. Lett. 2001, 3, 3761.
8. Cross-coupling reactions of arenediazonium salts, one of the attractive candidates for halogen-free electrophiles, have been extensively studied: a) K. Kikukawa, K. Kono, F. Wada, T. Matsuda, J. Org. Chem. 1983, 48, 1333; b) S. Sengupta, S. Bhattacharya, J. Org. Chem. 1997, 62, 3405; c) M. B. Andrus, C. Song, Org. Lett. 2001, 3, 3761.
9. This result is in sharp contrast to the fluoride ion-promoted Hiyama coupling in which aryldifluorosilanes are more reactive than aryltrifluorosilanes: Y. Hatanaka, K. Goda, Y. Okahara, T. Hiyama, Tetrahedron 1994, 50, 8301.
10. 2-carbon-nitrogen bond to the zero-valent palladium complex to form a cationic aryl-palladium intermediate. Then, transmetalation of the aryl substituent on the resulting pentacoordinate silicon atom and subsequent reductive elimination afford the biaryl product. (Equation Presented)
11. The role of the methanol has not been clarified at the present time, but it can be assumed that the oxygen atom of methanol coordinates to the silicon center to form a pentacoordinate silicon species, and the resulting acidic hydrogen atom on the methanol interacts with the nitrogen atom of the triazene to enhance the oxidative addition to palladium complex.
12. [4b,10a,11a]
13. [6]
14. Synthesis of symmetrical stilbene compounds via a double Heck reaction of arenediazonium salts, generated in situ from 1-aryltriazenes, with vinyltriethoxysilane has been reported: a) S. Sengupta, S. K. Sadhukhan, Org. Synth. 2002, 79, 52; b) S. Sengupta, S. Bhattacharyya, S. K. Sadhukhan, J. Chem. Soc. Parkin Trans. 1 1998, 275.
15. Synthesis of symmetrical stilbene compounds via a double Heck reaction of arenediazonium salts, generated in situ from 1-aryltriazenes, with vinyltriethoxysilane has been reported: a) S. Sengupta, S. K. Sadhukhan, Org. Synth. 2002, 79, 52; b) S. Sengupta, S. Bhattacharyya, S. K. Sadhukhan, J. Chem. Soc. Parkin Trans. 1 1998, 275.
16. It is widely accepted that the palladium-catalyzed coupling reaction of arenediazonium salts with vinylsilanes proceeds by a Mizoroki-Heck-type addition-elimination mechanism: a) K. Kikukawa, K. Ikenaga, F. Wada, T. Matsuda, Chem. Lett. 1983, 1337; b) K. Ikenaga, S. Matsumoto, K. Kikukawa, T. Matsuda, Chem. Lett. 1990, 185.
17. It is widely accepted that the palladium-catalyzed coupling reaction of arenediazonium salts with vinylsilanes proceeds by a Mizoroki-Heck-type addition-elimination mechanism: a) K. Kikukawa, K. Ikenaga, F. Wada, T. Matsuda, Chem. Lett. 1983, 1337; b) K. Ikenaga, S. Matsumoto, K. Kikukawa, T. Matsuda, Chem. Lett. 1990, 185.