Synthesis of tri- and diaryloxybenzenes by rhodium-catalyzed complete intermolecular [2+2+2] cycloaddition of aryl ethynyl ethers

Synlett

Volumn , Issue 20, 2010, Pages 3092-3098

  Komine, Yoshiyuki ^a   Miyauchi, Yuta ^a   Kobayashi, Masayuki ^a   Tanaka, Ken ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

2+2+2 cycloaddition; alkynes; aryl ethynyl ethers; H8 BINAP; rhodium

Indexed keywords

ALKYNYL GROUP; ARYLETHYNYL ETHER; BENZENE DERIVATIVE; DIARYLOXYBENZENE DERIVATIVE; RHODIUM; TRIARYLOXYBENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CYCLOADDITION; ROOM TEMPERATURE; SYNTHESIS;

EID: 78650175923     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259064     Document Type: Article

References (34)

1. For recent reviews of the transition-metal-catalyzed [2+2+2] cycloaddition reactions, see:, Galan B R., Rovis T, Angew. Chem. Int. Ed. 2009 48 2830
2. Tanaka K, Chem. Asian J. 2009 4 508
3. Varela J A., Saá C, Synlett 2008 2571
4. Shibata T, Tsuchikama K, Org. Biomol. Chem. 2008 1317
5. Heller B, Hapke M, Chem. Soc. Rev. 2007 36 1085
6. Agenet N, Buisine O, Slowinski F, Gandon V, Aubert C, Malacria M, Organic Reactions Vol. 68 RajanBabu T V. John Wiley and Sons Hoboken 2007 1
7. Chopade P R., Louie J, Adv. Synth. Catal. 2006 348 2307
8. Gandon V, Aubert C, Malacria M, Chem. Commun. 2006 2209
9. Kotha S, Brahmachary E, Lahiri K, Eur. J. Org. Chem. 2005 4741
10. Gandon V, Aubert C, Malacria M, Curr. Org. Chem. 2005 9 1699
11. Yamamoto Y, Curr. Org. Chem. 2005 9 503
12. Semmelhack M F., Park J, Organometallics 1986 5 2550
13. Suzuki D, Urabe H, Sato F, J. Am. Chem. Soc. 2001 123 7925
14. Takahashi T, JP 11263737 1999; Chem. Abstr. 1999, 131, 228541
15. For the transition-metal-mediated intermolecular [4+2]-benzannulation reactions using alkynyl ethers, see:, Darbasie N D., Schnatter W F. K., Warner K F., Manolache N, Tetrahedron Lett. 2006 47 963
16. Dudley G B., Takaki K S., Cha D D., Danheiser R L., Org. Lett. 2000 2 3407
17. Gevorgyan V, Quan L G., Yamamoto Y, J. Org. Chem. 2000 65 568
18. Morris K G., Saberi S P., Thomas S E., J. Chem. Soc., Chem. Commun. 1993 209
19. Danheiser R L., Brisbois R G., Kowalczyk J J., Miller R F., J. Am. Chem. Soc. 1990 112 3093
20. Danheiser R L., Gee S K., Perez J J., J. Am. Chem. Soc. 1986 108 806
21. For the nickel-catalyzed complete intermolecular cross-[2+2+2] cycloaddition of two ethyl ethynyl ethers and carbon dioxide, see:, Tsuda T, Kunisada K, Nagahama N, Morikawa S, Saegusa T, Synth. Commun. 1989 19 1575
22. For the rhodium-catalyzed complete intermolecular cross-[2+2+2] cycloaddition of two ethyl ethynyl ethers with an isocyanate, see:, Oberg K M., Lee [nl]E E., Rovis T, Tetrahedron 2009 65 5056
23. For the nickel-catalyzed complete intermolecular cross-[3+2+2] cycloaddition of ethyl cyclopropylideneacetate, an internal 1,3-diyne, and an alkynyl ether, see:, Yamasaki R, Terashima N, Sotome I, Komagawa S, Saito S, J. Org. Chem. 2010 75 480
24. Komine Y, Tanaka K, Org. Lett. 2010 12 1312
25. For the rhodium-catalyzed [2+2+2] cycloadditions of phenol-linked 1,6-diynes with alkynes and nitriles, leading to substituted dibenzofurans and azadibenzofurans, see:, Komine Y, Kamisawa A, Tanaka K, Org. Lett. 2009 11 2361
26. Tri- and diaryloxybenzenes are useful compounds in material sciences. For selected recent examples, see:, Pei S, Chen X, Jiang Z, Peng W, J. Appl. Polym. Sci. 2010 117 2069
27. Yamanaka M, Fujii H, J. Org. Chem. 2009 74 5390
28. Chen X, Zhang Y, Liu B, Zhang J, Wang H, Zhang W, Chen Q, Pei S, Jiang Z, J. Mater. Chem. 2008 18 5019
29. Rao X, Dang G, Zhou H, Yang W, Cui G, Chen C, Yokota R, J. Polym. Sci., Part A: Polym. Chem. 2007 45 4844
30. Tanaka K, Shirasaka K, Org. Lett. 2003 5 4697
31. Tanaka K, Toyoda K, Wada A, Shirasaka K, Hirano M, Chem. Eur. J. 2005 11 1145
32. For our account of the cationic rhodium(I)-biaryl bisphosphine-complex- catalyzed [2+2+2]-cycloaddition reactions, see:, Tanaka K, Synlett 2007 1977
33. For the rhodium(I)-catalyzed [2+2+2] cycloaddition of diynes with internal alkynyl ethers, see:, Alayrac C, Schollmeyer D, Witulski B, Chem. Commun. 2009 1464
34. Clayden J, Moran W J., Org. Biomol. Chem. 2007 5 1028