Palladium/P(t-Bu)3-catalyzed synthesis of aryl t-butyl ethers and application to the first synthesis of 4-chlorobenzofuran

Tetrahedron Letters

Volumn 40, Issue 50, 1999, Pages 8837-8840

  Watanabe, Makoto ^a   Nishiyama, Masakazu ^a   Koie, Yasuyuki ^a  

^a TOSOH CORPORATION   (Japan)

Author keywords

Alkoxylation; Aryl halides; Benzofurans; Ethers; Palladium catalysts

Indexed keywords

4 CHLOROBENZOFURAN; BENZOFURAN DERIVATIVE; ETHER DERIVATIVE; HALIDE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033544816     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01855-9     Document Type: Article

References (28)

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17. 3 showed the same reactivity and selectivity.
18. t-Butyl(dimethyl)silyl aryl ether was also obtained by reaction between TBDMSONa and 4-bromobenzophenone in 94% yield.
19. This case resulted in the by-production of 10% yield of t-butyl p-chlorobenzoate which may arise from β-hydride elimination of a Pd-hemiacetal intermediate from reaction of the aldehyde group with t-butoxide.
20. 2 and BINAP gave a sluggish reaction of 2,6-dichlorotoluene with t-BuONa and lost its catalytic activity at 10% conversion of the substrate at 120°C.
21. (a) Ota, T.; Hasegawa, S.; Inoue, S.; Sato, K. J. Chem. Soc., Perkin Trans. 1 1988, 3029.
22. (b) Ito, Y.; Aoyama, T.; Shioiri, T. Synlett 1997, 1163.
23. 3): δ=45.90, 128.27, 129.34, 129.86, 136.14, 196.71.
24. When the acetal protected by ethylene glycol was used instead of 1, the ratio of the desired product:dechlorinated products decreased to 5.0:1.
25. 4 gave only a trace amount of 4-chlorobenzofuran.
26. 3): δ=105.40, 110.09, 122.78, 124.92, 126.33, 127.04, 145.49, 155.31.
27. 3-ligated palladium on animation of aryl halides (Ref. ), biaryl synthesis based on Suzuki couplings and vinylation of aryl halides were reported using the same catalytic system, see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 1998, 37, 3387 for Suzuki coupling, and Littke, A. F.; Fu, G. C.J. Org. Chem. 1999, 64, 10 for vinylation.
28. 3-ligated palladium on animation of aryl halides (Ref. ),biaryl synthesis based on Suzuki couplings and vinylation of aryl halides were reported using the same catalytic system,see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 1998, 37, 3387 for Suzuki coupling, and Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10 for vinylation.